toluene-4-sulfonic acid (S)-2-cyclopropyl-2-hydroxy-ethyl ester | 615251-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid (S)-2-cyclopropyl-2-hydroxy-ethyl ester
• 英文别名: (1S)-1-cyclopropyl-1-hydroxy-2-(4'-toluenesulfonyloxy)ethane；[(2S)-2-cyclopropyl-2-hydroxyethyl] 4-methylbenzenesulfonate
• CAS: 615251-46-2
• 化学式: C₁₂H₁₆O₄S
• 分子量: 256.323
• InChiKey: KOEVLRJOHDQWAG-GFCCVEGCSA-N

物化性质

• 沸点：
  420.0±28.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid (S)-2-cyclopropyl-2-hydroxy-ethyl ester 、 叔丁基二甲基氯硅烷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c
• 作为产物：
  描述：

  (S)-1-cyclopropyl-ethane-1,2-diol 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到toluene-4-sulfonic acid (S)-2-cyclopropyl-2-hydroxy-ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Iclaprim Enantiomers―A Versatile Approach to 2-Substituted Chiral Chromenes

  摘要：

  Both enantiomers of the DHFR inhibitor iclaprim (R)-1 and (5)-1 were synthesized from the cyclopropyl homoallyl alcohols (R)-6 and (S)-6. respectively. As key steps these transformations include a Mitsunobu reaction and the formation of the diaminopyrimidine unit prior to a novel cyclization procedure to obtain the desired chromene heterocycle. The moderate enantioselectivity of the products (R)-1 and OH is related to the Mitsunobu reaction, which unfortunately did not proceed with complete inversion or configuration.

  DOI：

  10.1021/jo100566c

文献信息

• Preparation of 24 alkyl analogs of cholecalciferol and non-racemic compounds
  申请人：Kutner Andrzej

  公开号：US20050119241A1

  公开（公告）日：2005-06-02

  Disclosed is a process for the preparation of 24-alkyl analogs of cholecalcyferol of Formula 1 having a (5E) or (5Z) configuration, wherein X represents a hydrogen atom, a hydroxy group or an OR 1 group, where R 1 , R 2 and R 3 may be the same or different and represent groups suitable for hydroxyl protection, and R 4 is a C 1-6 alkyl chain or a C 1-6 cykloalkyl group, optionally substituted with C 1-3 alkyl groups, especially for calcipotriol. The invention also provides new intermediates and non-racemic compounds being valuable synthones for the synthesis of pharmacologically active substances.

  本发明揭示了一种制备具有(5E)或(5Z)构型的胆钙醇24-烷基类似物的方法，其中X代表氢原子、羟基或OR1基团，其中R1、R2和R3可以相同或不同，并表示适用于羟基保护的基团，而R4是C1-6烷基链或C1-6环烷基团，可选地被C1-3烷基取代，特别适用于骨化三醇。本发明还提供了新的中间体和非外消旋化合物，是合成药理活性物质的有价值的合成物。
• Identification of a Nonbasic Melanin Hormone Receptor 1 Antagonist as an Antiobesity Clinical Candidate
  作者：William N. Washburn、Mark Manfredi、Pratik Devasthale、Guohua Zhao、Saleem Ahmad、Andres Hernandez、Jeffrey A. Robl、Wei Wang、James Mignone、Zhenghua Wang、Khehyong Ngu、Mary Ann Pelleymounter、Daniel Longhi、Rulin Zhao、Bei Wang、Ning Huang、Neil Flynn、Anthony V. Azzara、Joel C. Barrish、Kenneth Rohrbach、James J. Devenny、Suzanne Rooney、Michael Thomas、Susan Glick、Helen E. Godonis、Susan J. Harvey、Mary Jane Cullen、Hongwei Zhang、Christian Caporuscio、Paul Stetsko、Mary Grubb、Brad D. Maxwell、Hong Yang、Atsu Apedo、Brian Gemzik、Evan B. Janovitz、Christine Huang、Lisa Zhang、Chris Freeden、Brian J. Murphy

  DOI：10.1021/jm500026w

  日期：2014.9.25

  Identification of MCHR1 antagonists with a preclinical safety profile to support clinical evaluation as antiobesity agents has been a challenge. Our finding that a basic moiety is not required for MCHR1 antagonists to achieve high affinity allowed us to explore structures less prone to off-target activities such as hERG inhibition. We report the SAR evolution of hydroxylated thienopyrimidinone ethers culminating in the identification of 27 (BMS-819881), which entered obesity clinical trials as the phosphate ester prodrug 35 (BMS-830216).
• [EN] PREPARATION OF 24 ALKYL ANALOGS OF CHOLECALCIFEROL AND NON-RACEMIC COMPOUNDS<br/>[FR] PREPARATION D'ANALOGUES ALKYL-24 DE CHOLECALCIFEROL ET DE COMPOSES NON RACEMIQUES
  申请人：——

  公开号：WO2003087048A3

  公开（公告）日：2004-03-18
• PREPARATION OF 24-ALKYL ANALOGS OF CHOLECALCIFEROL AND NON-RACEMIC COMPOUNDS
  申请人：INSTYTUT FARMACEUTYCZNY

  公开号：EP1497264A2

  公开（公告）日：2005-01-19
• US7915241B2
  申请人：——

  公开号：US7915241B2

  公开（公告）日：2011-03-29