(2R,4R)-(+)-2-(二苯基膦基甲基)-4-(二环己基膦基)-N-甲基-1-吡咯烷甲酰胺 | 122709-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2R,4R)-(+)-2-(二苯基膦基甲基)-4-(二环己基膦基)-N-甲基-1-吡咯烷甲酰胺
• 中文别名: (2R,4R) - (+)-2-(二苯基膦基甲基)-4 - (二环己基膦基)-N-甲基-1-吡咯烷甲酰胺
• 英文名称: (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine
• 英文别名: (2R,4R)-N-(methylcarbamoyl)-4-(dicyclohexylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine；(2R,4R)-N-methylcarbamoyl-4-dicyclohexylphosphino-2-diphenylphosphinomethylpyrrolidine；(2R,4R)-4-(dicyclohexyl-phosphino)-2-(diphenylphosphinomethyl)-N-methylaminocarbonyl-pyrrolidine；(2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonylpyrrolidine；(2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphinomethyl)-N-methylaminocarbonylpyrrolidine；(2R,4R)-4-dicyclohexylphosphino-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonylpyrrolidine；(2R,4R)-Mccpm；(2R,4R)-4-dicyclohexylphosphanyl-2-(diphenylphosphanylmethyl)-N-methylpyrrolidine-1-carboxamide
• CAS: 122709-72-2
• 化学式: C₃₁H₄₄N₂OP₂
• 分子量: 522.651
• InChiKey: BREAVWOTKQHAAN-FYBSXPHGSA-N

物化性质

• 沸点：
  678.8±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

SDS

---

Section 1: Product Identification
(2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4-(dicyclohexylphosphino)-N-methyl-1-pyrrolidinecarboxamide, min.
Chemical Name:
97% (R,R-MCCPM)
CAS Registry Number: 122709-72-2
Formula: C31H44N2OP2
EINECS Number: none
Chemical Family: organophosphine ligand
(R,R-MCCPM);
Synonym:
(2R,4R)-4-(dicyclohexylphosphino)-2-((diphenylphosphino)methyl)-N-methylpyrrolidine-1-carboxamide

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 122709-72-2 100% no data no data

---

Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

---

SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

---

SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

---

SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non-combustible adsorbent and
Spill and Leak Procedures:
swept up.

---

SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep in a cool, dry,
Handling and Storage:
well-ventillated area.

---

SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

---

SECTION 9: Physical and Chemical Properties
Color and Form: white powder
Molecular Weight: 522.64
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

---

SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged exposure to air
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, phorsphorous oxides and organic fumes

---

SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

---

SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

---

SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not reportable under SARA 313
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3'-(2-aminoacetyl)-4'-fluoromethanesulfonanilide hydrochloride 、 (2R,4R)-(+)-2-(二苯基膦基甲基)-4-(二环己基膦基)-N-甲基-1-吡咯烷甲酰胺 、 、 三乙胺 、 氢气 以 甲醇 为溶剂， 50.0 ℃ 、270.18 MPa 条件下， 以to give 15.8 g of crude (R)-(-)-3'-(2-amino-1-hydroxyethyl)-4'-fluoromethanesulfonanilide的产率得到N-[3-(2-氨基-1-羟基乙基)-4-氟苯基]甲烷磺酰胺
  参考文献：
  名称：

  Sulfonanilide derivatives and medicine

  摘要：

  本发明的目的是提供一种对尿道具有高选择性的治疗尿失禁的药剂。本发明的化合物之一是具有以下式子（I）的磺酰苯胺衍生物。## STR1 ## 本发明的化合物表现出对尿道平滑肌的选择性收缩作用，因此它们具有作为治疗尿失禁的药物的有用效果。

  公开号：

  US05360822A1
• 作为产物：
  描述：

  (2R,4R)-4-(dicyclohexylphosphinyl)-2-<(diphenylphosphinyl)methyl>pyrrolidine 在 三氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 (2R,4R)-(+)-2-(二苯基膦基甲基)-4-(二环己基膦基)-N-甲基-1-吡咯烷甲酰胺
  参考文献：
  名称：

  Efficient Asymmetric Hydrogenation of .ALPHA.-Amino Ketone Derivatives. A Highly Enantioselective Synthesis of Phenylephrine, Levamisole, Carnitine and Propranolol.

  摘要：

  吡咯烷双膦配体（CPMs）与铑（I）形成的复合物被发现是α-氨基酮 hydrochloride 衍生物的不对称加氢反应的高效催化剂。利用这一方法，我们开发了光学活性的β-氨基醇、苯肾上腺素、左旋咪唑、肉碱和普萘洛尔的高效不对称合成。

  DOI：

  10.1248/cpb.43.738
• 作为试剂：
  描述：

  3'-benzyloxy-2-(N-benzyl-N-methyl)aminoacetophenone hydrochloride 在 palladium on activated charcoal chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氢气 、 三乙胺 、 (2R,4R)-(+)-2-(二苯基膦基甲基)-4-(二环己基膦基)-N-甲基-1-吡咯烷甲酰胺 作用下， 以 甲醇 、 乙醇 为溶剂， 50.0 ℃ 、2.03 MPa 条件下， 反应 23.0h， 生成 盐酸去氧肾上腺素
  参考文献：
  名称：

  Efficient Asymmetric Hydrogenation of .ALPHA.-Amino Ketone Derivatives. A Highly Enantioselective Synthesis of Phenylephrine, Levamisole, Carnitine and Propranolol.

  摘要：

  吡咯烷双膦配体（CPMs）与铑（I）形成的复合物被发现是α-氨基酮 hydrochloride 衍生物的不对称加氢反应的高效催化剂。利用这一方法，我们开发了光学活性的β-氨基醇、苯肾上腺素、左旋咪唑、肉碱和普萘洛尔的高效不对称合成。

  DOI：

  10.1248/cpb.43.738

文献信息

• [DE] VERKÜRZTES VERFAHREN ZUR HERSTELLUNG VON L-LOBELIN<br/>[EN] SHORTENED METHOD FOR THE PRODUCTION OF L-LOBELINE<br/>[FR] PROCEDE RACCOURCI POUR LA PRODUCTION DE L-LOBELINE
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2006008029A1

  公开（公告）日：2006-01-26

  Die vorliegende Erfindung betrifft ein verkürztes Verfahren zur Herstellung von L-Lobelin mittels Rhodium-katalysierter asymmetrischer Hydrierung im industriellen Maßstab.

  这项发明涉及一种在工业规模下利用铑催化的不对称氢化缩短制备L-Lobelin的方法。
• [EN] METHOD FOR PRODUCING AMIDINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS D'AMIDINE
  申请人：BIOCRYST PHARM INC

  公开号：WO2016029216A2

  公开（公告）日：2016-02-25

  The invention provides methods and intermediates useful in the synthesis of a compound of formula (I): or a pharmaceutically acceptable salt, solvate, ester or prodrug thereof; wherein the variables are as defined herein.

  本发明提供了用于合成式(I)化合物的方法和中间体，或其药学上可接受的盐、溶剂和前药酯；其中变量如本文所定义。
• Sulfonanilide derivatives and medicine
  申请人：Nippon Shinyaku Co. Ltd.

  公开号：US05360822A1

  公开（公告）日：1994-11-01

  An object of the present invention is to offer an agent for curing urinary incontinence with high selectivity for the urethra. One of the compounds of the present invention is a sulfonanilide derivative having the following formula (I). ##STR1## The compounds of the present invention exhibit selective contracting action to smooth muscle of the urethra tract whereupon they have useful effect as remedies for urinary incontinence.

  本发明的目的是提供一种对尿道具有高选择性的治疗尿失禁的药剂。本发明的化合物之一是具有以下式子（I）的磺酰苯胺衍生物。## STR1 ## 本发明的化合物表现出对尿道平滑肌的选择性收缩作用，因此它们具有作为治疗尿失禁的药物的有用效果。
• Process for manufacturing of chiral lobelin
  申请人：Klingler Franz-Dietrich

  公开号：US20060014791A1

  公开（公告）日：2006-01-19

  The present invention relates to a shortened process for preparing L-lobeline by rhodium-catalysed asymmetric hydrogenation on an industrial scale.

  本发明涉及一种缩短工业规模上通过铑催化不对称氢化制备L-洛贝林的过程。
• New chiral phosphinopyrrolidine compounds and their use for asymetric synthesis of optically active compounds
  申请人：Achiwa, Kazuo

  公开号：EP0251164A2

  公开（公告）日：1988-01-07

  New chiral phosphinopyrrolidine compounds of the general formula: or wherein R1 is a hydrogen atom, -COR, -COOR, -CONHR or -SO2R where R is an alkyl or aryl group, R2 and R3 each represents independently an aryl group which may have a substituent or substituents, and RA and R5 each represents independently an aliphatic or cycloaliphatic hydrocarbyl group which may have a substituent or substituents, as well as the use of these compound as ligand for a metal complex catalyst for asymmetric synthesis or optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.

  通式如下的新型手性膦基吡咯烷化合物 或 其中 R1 是氢原子、-COR、-COOR、-CONHR 或 -SO2R 其中 R 是烷基或芳基，R2 和 R3 分别独立地代表芳基（可带有一个或多个取代基），RA 和 R5 分别独立地代表脂肪族或环脂族烃基（可带有一个或多个取代基）。新的手性膦基吡咯烷化合物是一种有用的配体，在催化不对称还原反应中可获得高光学产率和高反应效率。