(3R,5R)-(-)-3,5-庚二醇 | 77291-90-8

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3R,5R)-(-)-3,5-庚二醇
• 中文别名: (3R,5R)-(-)-3,5-庚烷二醇
• 英文名称: (R,R)-3,5-Heptanediol
• 英文别名: (3R,5R)-Heptane-3,5-diol
• CAS: 77291-90-8
• 化学式: C₇H₁₆O₂
• 分子量: 132.203
• InChiKey: BQWORYKVVNTRAW-RNFRBKRXSA-N

物化性质

• 熔点：
  52-53℃
• 比旋光度：
  -40° (c 10, ethanol)
• 沸点：
  110℃ (12 Torr)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2905399090

SDS

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Section 1: Product Identification
Chemical Name: (3R,5R)-(-)-3,5-Heptanediol, 99%
CAS Registry Number: 77291-90-8
Formula: C7H16O2
EINECS Number: none
Chemical Family: organic alcohol
Synonym: (3R,5R)-(-)-Heptane-3,5-diol

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 77291-90-8 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Causes irritation of the eyes.
Skin Contact: Causes irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion.
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

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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.

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SECTION 5: Fire Fighting Measures
Flash Point: none
Autoignition Temperature: none
Explosion Limits: none
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 toxic and irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep in a cool, dry, well ventilated place.

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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.

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SECTION 9: Physical and Chemical Properties
Color and Form: colorless solid
Molecular Weight: 132.20
Melting Point: 52°
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide and organic fumes.

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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

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SECTION 12: Ecological Information
Ecological Information: No information available

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

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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

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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (3R,5R)-(-)-3,5-庚二醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 61.0h， 生成 (R,R)-N-benzyl-2,4-diethylazetidine
  参考文献：
  名称：

  2,4-二取代氮杂环丁烷的对映选择性制备

  摘要：

  手性 C2 对称 N-苄基氮杂环丁烷可以方便地从光学纯的抗 1,3-二醇制备，而不会损失对映体纯度。N-脱苄基化生成相应的 N-未取代氮杂环丁烷，然后将其与芳基溴化物进行钯催化偶联反应，得到手性 N-芳基氮杂环丁烷。(R,R)-N-Benzyl-2,4-二甲基氮杂环丁烷已用于合成新的环钯络合物，例如，可用作磷配体的手性识别剂。

  DOI：

  10.1002/(sici)1099-0690(200005)2000:9<1815::aid-ejoc1815>3.0.co;2-8
• 作为产物：
  描述：

  3,5-庚烷二酮 在 [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) 氢溴酸 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、6.67 kPa 条件下， 反应 70.0h， 生成 (3R,5R)-(-)-3,5-庚二醇
  参考文献：
  名称：

  2,4-二取代氮杂环丁烷的对映选择性制备

  摘要：

  手性 C2 对称 N-苄基氮杂环丁烷可以方便地从光学纯的抗 1,3-二醇制备，而不会损失对映体纯度。N-脱苄基化生成相应的 N-未取代氮杂环丁烷，然后将其与芳基溴化物进行钯催化偶联反应，得到手性 N-芳基氮杂环丁烷。(R,R)-N-Benzyl-2,4-二甲基氮杂环丁烷已用于合成新的环钯络合物，例如，可用作磷配体的手性识别剂。

  DOI：

  10.1002/(sici)1099-0690(200005)2000:9<1815::aid-ejoc1815>3.0.co;2-8

文献信息

• Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid
  作者：Jun-ichi Matsuo、Yu Hattori、Mio Hashizume、Hiroyuki Ishibashi

  DOI：10.1016/j.tet.2010.06.012

  日期：2010.8

  Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99%

  通过使用抗-1,3-二醇和催化量的苯中的2,4-二硝基苯磺酸（DNBSA），在回流下将脂肪族酮还原为相应的仲醇。在该介质中加入1-辛硫醇可提高还原效率。通过使用手性抗戊烷-2,4-二醇进行脂族酮的不对称还原，并且在叔烷基酮的还原中观察到高度不对称的诱导作用（最高> 99％ee）。在不存在辛硫醇的情况下，使用手性抗戊烷-2,4-二醇和DNBSA进行的酰基硅烷的不对称还原有效地进行，并以高收率和高ee收率获得了相应的α-甲硅烷基醇。
• The Stereo-differentiating (Asymmetric) Hydrogenation of the C=O Double Bond with a Modified Nickel Catalyst. XXXV. A Facile Method for the Preparation of Optically Pure β-Diols
  作者：Kazuhisa Ito、Tadao Harada、Akira Tai

  DOI：10.1246/bcsj.53.3367

  日期：1980.11

  The hydrogenation of RCOCH2COR over a Raney nickel catalyst modified with a mixture of tartaric acid and NaBr gave (R*, R*-RCH(OH)CH2CH(OH)R selectively with a high optical purity. The substrates with R=CH3–, CH3CH2–, CH3CH2CH2–, CH3(CH2)4CH2–, and Ph– were employed in this study. In all cases, the recrystallization of the hydrogenation product gave an optically pure (R*,R*)-isomer which was free from the (R*,S*)-isomer.

  在改性了酒石酸和NaBr混合物的Raney镍催化剂上，对RCOCH2COR进行氢化反应，得到了光学纯度较高的(R*, R*-RCH(OH)CH2CH(OH)R选择性产物。该研究中使用的底物包括R=CH3–、CH3CH2–、CH3CH2CH2–、CH3(CH2)4CH2–以及Ph–。在所有情况下，氢化产物的再结晶得到的都是光学纯的(R*,R*)-异构体，且不含(R*,S*)-异构体。
• Ruthenium(<scp>II</scp>)–BINAP catalysed stereoselective homogeneous hydrogenation of 1,3-diketones
  作者：Hiroyuki Kawano、Youichi Ishii、Masahiko Saburi、Yasuzo Uchida

  DOI：10.1039/c39880000087

  日期：——

  Ruthenium–BINAP catalysed hydrogenation of 1,3-diketones gives 1,3-diols with extremely high diastereo- and enantio-selectivity.

  钌–BINAP催化的1,3-二酮加氢生成1,3-二醇，具有极高的非对映选择性和对映选择性。
• Highly diastereoselective Markovnikov hydration of 3,4-dialkoxy-1-alkenes and 4,5-dialkoxy-2-alkenes via a hydroboration-oxidation process
  作者：Michael E. Jung、Usama Karama

  DOI：10.1016/s0040-4039(99)01496-3

  日期：1999.11

  Hydroboration-oxidation of 3,4-dialkoxy- and 3,4,5-trialkoxy-1-alkenes and 4,5-dialkoxy-2-alkenes occurs to give high proportions of the secondary alcohols (Markovnikov hydration) with excellent diastereoselectivity (anti to the allylic alkoxide). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Blanc, Delphine; Ratovelomanana-Vidai, Virginie; Marinetti, Angela, Synlett, 1999, # 4, p. 480 - 482
  作者：Blanc, Delphine、Ratovelomanana-Vidai, Virginie、Marinetti, Angela、Genêt, Jean-Pierre

  DOI：——

  日期：——