(S,S’,R,R’)-TangPhos | 752258-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: (S,S’,R,R’)-TangPhos
• 英文别名: (1R,2S)-1-tert-butyl-2-[(1R,2S)-1-tert-butylphospholan-2-yl]phospholane
• CAS: 752258-19-8
• 化学式: C₁₆H₃₂P₂
• 分子量: 286.378
• InChiKey: SJNUZTRUIDRSJK-LBTBCDHLSA-N

物化性质

• 沸点：
  353.6±12.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (S,S’,R,R’)-TangPhos 、 [Co(CH2SiMe3)2(pyridine)2] 以 乙醚 为溶剂， 生成 (1S,1’S,1R,1’R)-(TangPhos)Co(CH₂SiMe₃)₂
  参考文献：
  名称：

  WO2023/114458

  摘要：

  公开号：
• 作为试剂：
  描述：

  N-[1-(5-bromo-3-fluoropyridin-2-yl)vinyl]acetamide 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (S,S’,R,R’)-TangPhos 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、690.01 kPa 条件下， 反应 4.33h， 以97%的产率得到N-[(1R)-1-(5-bromo-3-fluoropyridin-2-yl)ethyl]acetamide
  参考文献：
  名称：

  Practical Synthesis of a Potent Bradykinin B₁ Antagonist via Enantioselective Hydrogenation of a Pyridyl N-Acyl Enamide

  摘要：

  A practical and efficient synthesis of bradykinin B I antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of I in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.

  DOI：

  10.1021/jo802772d

文献信息

• Preparation of eslicarbazepine and related compounds by asymmetric hydrogenation
  申请人：Yu Bing

  公开号：US20100173893A1

  公开（公告）日：2010-07-08

  A process for preparing a compound of the formula IA or IB: wherein R is alkyl, aminoalkyl, halogenalkyl, aralkyl, cycloalkyl, cycloalkylalkyl, alkoxy, phenyl or substituted phenyl or pyridyl group; the term alkyl means carbon chain, straight or branched, containing from 1 to 18 carbon atoms; the term halogen represents fluorine, chlorine, bromine or iodine; the term cycloalkyl represents a saturated alicyclic group with 3 to 6 carbon atoms; the term aryl represents unsubstituted phenyl group or phenyl substituted by alkoxy, halogen or nitro group, the process comprising asymmetric hydrogenation of a compound of the formula II: wherein R has the same meanings as above, using a chiral catalyst and a source of hydrogen.

  一种制备式为IA或IB的化合物的方法：其中R是烷基，氨基烷基，卤代烷基，芳基烷基，环烷基，环烷基烷基，烷氧基，苯基或取代苯基或吡啶基；术语烷基表示碳链，直链或支链，含有1至18个碳原子；术语卤素代表氟，氯，溴或碘；术语环烷基表示具有3至6个碳原子的饱和脂环族基；术语芳基表示未取代的苯基或被烷氧基，卤素或硝基取代的苯基，该方法包括使用手性催化剂和氢源对式为II的化合物进行不对称氢化反应，其中R具有与上述相同的含义。
• Process For the Preparation of Enantiomerically Pure1-Substitued-3-Aminoalcohols
  申请人：Michel Dominique

  公开号：US20080154047A1

  公开（公告）日：2008-06-26

  A process for the preparation of enantiomerically pure 1-substituted-3-amino-alcohols, particularly of (S)-(−)- and (R)-(+)-3-N-methylamino-1-(2-thienyl)-1-propanol, by asymmetrically hydrogenating salts of a carboxylic acids with an aminoketone of the formula: wherein R 1 is 2-thienyl, 2-furanyl or phenyl, each optionally substituted with one or more halogen atoms and/or one or more C 1-4 -alkyl or C 1-4 -alkoxy groups, and wherein R 2 is C 1-4 -alkyl or phenyl, each optionally substituted with one or more halogen atoms and/or one or more C 1-4 -alkyl or C 1-4 -alkoxy groups. The corresponding aminoalcohols are obtained by subsequent hydrolysis of their salts. Salts of a carboxylic acid with the aminoketones and the aminoalcohols obtained by asymmetrically hydrogenating the aminoketones, respectively.

  一种制备对映纯1-取代-3-氨基醇的方法，特别是(S)-(-)-和(R)-(+)-3-N-甲基氨基-1-(2-噻吩基)-1-丙醇，通过将羧酸的盐与式中的氨基酮不对称加氢，其中R1为2-噻吩基、2-呋喃基或苯基，每个均可选地取代有一个或多个卤素原子和/或一个或多个C1-4-烷基或C1-4-烷氧基，而R2为C1-4-烷基或苯基，每个均可选地取代有一个或多个卤素原子和/或一个或多个C1-4-烷基或C1-4-烷氧基。相应的氨基醇可通过其盐的后续水解获得。羧酸的盐与氨基酮以及通过不对称加氢氨基酮获得的氨基醇的盐。
• Process for the preparation of enantiomerically pure 1-substituted-3-aminoalcohols
  申请人：Michel Dominique

  公开号：US20110207946A1

  公开（公告）日：2011-08-25

  Provided is a process for the preparation of enantiomerically pure 1-substituted-3-aminoalcohols, particularly of (S)-(−)- and (R)-(+)-3-N-methylamino-1-(2-thienyl)-1-propanol, by asymmetrically hydrogenating salts of a carboxylic acids with an aminoketone of formula (II), wherein R 1 is selected from the group consisting of 2-thienyl, 2-furanyl and phenyl, each optionally substituted with one or more halogen atoms and/or one or more C 1-4 -alkoxy groups, and wherein R 2 is C 1-4 -alkyl or phenyl, each optionally substituted with one or more halogen atoms and/or one or more C 1-4 -alkyl or C 1-4 -alkoxy groups, and wherein the corresponding aminoalcohols are obtained by subsequent hydrolysis of their salts. Furthermore provided are salts of a carboxylic acid with said aminoketones and the aminoalcohols obtained by asymmetriacally hydrogenating said aminoketones, respectively.

  提供了一种制备对映纯的1-取代-3-氨基醇的方法，特别是(S)-(-)-和(R)-(+)-3-N-甲基氨基-1-(2-噻吩基)-1-丙醇，通过对式(I)的氨基酮进行不对称氢化羧酸盐，其中R1选自2-噻吩基、2-呋喃基和苯基的群，每个群可选择地取代一个或多个卤素原子和/或一个或多个C1-4-烷氧基，其中R2是C1-4-烷基或苯基，每个群可选择地取代一个或多个卤素原子和/或一个或多个C1-4-烷基或C1-4-烷氧基，相应的氨基醇通过其盐的后续水解得到。此外，还提供了羧酸盐与所述氨基酮的盐以及通过不对称氢化所述氨基酮得到的氨基醇。
• PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY PURE 1-SUBSTITUTED-3-AMINOALCOHOLS
  申请人：Brieden Walter

  公开号：US20120316350A1

  公开（公告）日：2012-12-13

  A process for the preparation of N-monosubstituted β-aminoalcohol sulfonates of formula (1a), (1b): wherein R 1 is C 6-20 -aryl or C 4-12 -heteroaryl, each optionally being substituted with one or more halogen atoms and/or one or more C 1-4 -alkyl or C 1-4 -alkoxy groups, R 2 is C 1-4 -alkyl or C 6-20 -aryl, each aryl optionally being substituted with one or more halogen atoms and/or one or more C 1-4 -alkyl or C 1-4 -alkoxy groups, and wherein R 3 is selected from the group consisting of C 1-18 -alkyl, C 6-20 -cycloalkyl, C 6-20 -aryl and C 7-20 -aralkyl residues; including a) reacting a methyl ketone, a primary amine, formaldehyde and a sulfonic acid, at a pressure above 1.5 bar, optionally in a organic solvent, said organic solvent which can include water to provide N-monosubstituted β-aminoketone sulfonates of formula (II): wherein R 1 , R 2 and R 3 are as defined above, and b) asymmetrically hydrogenating.

  一种制备式(1a)、(1b)的N-单取代β-氨基醇磺酸盐的方法，其中R1为C6-20芳基或C4-12杂芳基，每个芳基可选择性地被一个或多个卤素原子和/或一个或多个C1-4烷基或C1-4烷氧基取代，R2为C1-4烷基或C6-20芳基，每个芳基可选择性地被一个或多个卤素原子和/或一个或多个C1-4烷基或C1-4烷氧基取代，而R3从C1-18烷基、C6-20环烷基、C6-20芳基和C7-20芳基烷基残基中选择；包括a)在压力高于1.5巴的条件下，选择性地在有机溶剂中反应甲基酮、一级胺、甲醛和磺酸，所述有机溶剂可包括水，从而提供式(II)的N-单取代β-氨基酮磺酸盐：其中R1、R2和R3如上所定义；b)不对称氢化。
• US7973182B2
  申请人：——

  公开号：US7973182B2

  公开（公告）日：2011-07-05