R-2-hydroxy-4-phenylbutyric acid L-menthyl ester | 110143-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: R-2-hydroxy-4-phenylbutyric acid L-menthyl ester
• 英文别名: D-2-hydroxy-4-phenyl-butyric acid-((1R)-menthyl ester)；D-2-Hydroxy-4-phenyl-buttersaeure-((1R)-3c-methyl-6t-isopropyl-cyclohexyl-(r)-ester)；D-2-Hydroxy-4-phenyl-buttersaeure-((1R)-menthylester)；(L)-menthyl (R)-2-hydroxy-4-phenylbutyrate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-2-hydroxy-4-phenylbutanoate
• CAS: 110143-66-3
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: XUALAKZCTMSXQK-QXCFHYIPSA-N

物化性质

• 沸点：
  439.4±33.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  R-2-hydroxy-4-phenylbutyric acid L-menthyl ester 在 吡啶 、 盐酸 、 氢氧化钾 、 硫酸 、 sodium hydride 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.5h， 生成 盐酸替莫普利
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. Perhydro-1,4-thiazepin-5-one derivatives

  摘要：

  alpha-[6-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-5-oxoperhydro -1,4-thiazepin-4-yl]acetic acids (monoester monoacids) and their dicarboxylic acids having the hydrophobic substituents at the 2- or 3-position of the thiazepinone ring were prepared and assayed for angiotensin-converting enzyme (ACE) inhibitory activity. The dicarboxylic acids having the pseudoequatorial amino groups at the 6-position and the pseudoequatorial hydrophobic substituents at the 2- or 3-position of the chair conformation of the thiazepinone ring had potent in vitro inhibitory activity. The monoester monoacids having the hydrophobic substituents at the 2-position suppressed pressor response to angiotensin I for a longer duration than those having the substituents at the 3-position when administered orally. The structure-activity relationship was studied by conformational energy calculations of the thiazepinone ring.

  DOI：

  10.1021/jm00394a009
• 作为产物：
  描述：

  (L)-menthyl 2-oxo-4-phenylbutyrate 在 氢气 作用下， 以 乙醇 、 水 为溶剂， 50.0 ℃ 、1.0 MPa 条件下， 以62.4%的产率得到R-2-hydroxy-4-phenylbutyric acid L-menthyl ester
  参考文献：
  名称：

  一种（R）-2-羟基-4-苯基丁酸的制备方法

  摘要：

  本发明公开了一种（R）‑2‑羟基‑4‑苯基丁酸的制备方法，它包括以下步骤：在醇体系中2‑氧代‑4‑苯基丁酸‑L‑薄荷酯通过催化还原得到（R）‑2‑羟基‑4‑苯基丁酸‑L‑薄荷酯，（R）‑2‑羟基‑4‑苯基丁酸‑L‑薄荷酯通过水解、洗涤、萃取、重结晶得到（R）‑2‑羟基‑4‑苯基丁酸。本发明不但反应时间短，而且成品率高。

  公开号：

  CN106866402B

文献信息

• Process for making and isolating (R)-2-hydroxy-4-phenylbutyric acid and
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04837354A1

  公开（公告）日：1989-06-06

  Disclosed herein is a novel compound, (L)-menthyl 2-oxo-4-phenylbutyrate, and an improved process for making and isolating a substantially pure compound of the structural formula: ##STR1## wherein Y is hydrogen or (L)-menthyl the improvement which comprises: (a) stereoselectively reducing (L)-menthyl 2-oxo-4-phenylbutyrate by contacting said compound with S-B-(3-pinanyl)-9 horabicyclo[3,3,1]nonone, (b) stereoselectively isolating (L)-menthyl-(R)-2-hydroxy-4-phenylbutyrate by crystallization, and optionally hydrolyzing the so obtained ester; and further comprises optionally esterifying the so obtained acid by contacting said acid with a C.sub.1 -C.sub.6 alkanol in presence of acid.

  本文披露了一种新化合物，(L)-薄荷醇2-氧代-4-苯基丁酸酯，以及制备和分离结构式如下的基本纯化化合物的改进方法：##STR1## 其中Y为氢或(L)-薄荷醇，改进方法包括：(a)通过将化合物与S-B-(3-pinanyl)-9 horabicyclo[3,3,1]nonone接触来立体选择性地还原(L)-薄荷醇2-氧代-4-苯基丁酸酯，(b)通过结晶立体选择性地分离(L)-薄荷醇-(R)-2-羟基-4-苯基丁酸酯，并且可以水解所得酯；进一步包括通过在酸的存在下将所得酸与C.sub.1-C.sub.6烷醇接触来选用酯化所得酸。
• Biquard, Annales de Chimie (Cachan, France), 1933, vol. <10> 20, p. 97,113
  作者：Biquard

  DOI：——

  日期：——
• “An efficient synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate: A useful intermediate in the synthesis of converting enzymeinhibitors”
  作者：Gary A. Flynn、Douglas W. Beight

  DOI：10.1016/s0040-4039(00)80112-4

  日期：1988.1
• YANAGISAWA, HIROAKI;ISHIHARA, SADAO;ANDO, AKIKO;KANAZAKI, TAKURO;MIYAMOTO+, J. MED. CHEM., 30,(1987) N 11, 1984-1991
  作者：YANAGISAWA, HIROAKI、ISHIHARA, SADAO、ANDO, AKIKO、KANAZAKI, TAKURO、MIYAMOTO+

  DOI：——

  日期：——