(R)-3-(4-methoxyphenylthio)-4,4,4-trifluorobutanoic acid | 851371-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3-(4-methoxyphenylthio)-4,4,4-trifluorobutanoic acid
• 英文别名: (3R)-4,4,4-trifluoro-3-(4-methoxyphenyl)sulfanylbutanoic acid
• CAS: 851371-16-9
• 化学式: C₁₁H₁₁F₃O₃S
• 分子量: 280.268
• InChiKey: XJHPEETZLNDEGX-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-methoxyphenylthio)-4,4,4-trifluorobutanoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  碱催化的非对映异构体硫杂-迈克尔加成到手性 β-三氟甲基-α,β-不饱和 N-酰化恶唑烷-2-酮

  摘要：

  报道了硫醇与手性 β-三氟甲基-α,β-不饱和N-酰化恶唑烷-2-酮的碱催化非对映发散硫杂-迈克尔加成反应。通过调整碱催化剂（i -Pr 2 NEt、DABCO 或 P 2 - t -Bu），以良好的收率和高非对映选择性合成了一系列手性硫杂-迈克尔加合物。根据实验结果提出了一种合理的机制。这项工作是对现有方法的补充，提供了一些优点，例如，使用易于合成的手性起始材料、廉价且易于获得的碱催化剂、以及简单实用的操作来实现可切换的非对映选择性，使得能够在有机合成中进行合成应用。

  DOI：

  10.1039/d3ob00999h
• 作为产物：
  描述：

  (R)-ethyl 3-(4-methoxyphenylthio)-4,4,4-trifluorobutanoate 在 盐酸 、 水 作用下， 以90%的产率得到(R)-3-(4-methoxyphenylthio)-4,4,4-trifluorobutanoic acid
  参考文献：
  名称：

  Organocatalytic Asymmetric Sulfa-Michael Addition of Thiols to 4,4,4-Trifluorocrotonates

  摘要：

  The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-gamma-trifluoromethyl gamma-sulfone hydroxamate.

  DOI：

  10.1021/ol201766k

文献信息

• Novel highly potent, structurally simple γ-trifluoromethyl γ-sulfone hydroxamate inhibitor of stromelysin-1 (MMP-3)
  作者：Monica Sani、Gabriele Candiani、Françoise Pecker、Luciana Malpezzi、Matteo Zanda

  DOI：10.1016/j.tetlet.2005.02.063

  日期：2005.4

  The gamma-trifluoromethyl gamma-sulfone hydroxamate 1 was synthesized both in racemic and enantiomerically pure forms by means of a thia-Michael reaction of p-methoxythiophenol on achiral and chiral 3,3,3-trifluorocrotonoyl Michael acceptors. The (R)-1 enantiomer was the most potent inhibitor of MMP-3 (stromelysin-1), showing an IC50 = 3.2 nM, as well as the most selective with respect to MMP-9 (65-fold). (c) 2005 Elsevier Ltd. All rights reserved.
• Organocatalytic Asymmetric Sulfa-Michael Addition of Thiols to 4,4,4-Trifluorocrotonates
  作者：Xiu-Qin Dong、Xin Fang、Chun-Jiang Wang

  DOI：10.1021/ol201766k

  日期：2011.8.19

  The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-gamma-trifluoromethyl gamma-sulfone hydroxamate.
• Base-catalyzed diastereodivergent thia-Michael addition to chiral β-trifluoromethyl-α,β-unsaturated <i>N</i>-acylated oxazolidin-2-ones
  作者：Sasirome Racochote、Phiphob Naweephattana、Panida Surawatanawong、Chutima Kuhakarn、Pawaret Leowanawat、Vichai Reutrakul、Darunee Soorukram

  DOI：10.1039/d3ob00999h

  日期：——

  DABCO, or P2-t-Bu), a range of chiral thia-Michael adducts was synthesized in good yields with high diastereoselectivities. A plausible mechanism was proposed on the basis of the experimental results. This work is complementary to the existing methods offering advantages, e.g., switchable diastereoselectivity using a readily synthesized chiral starting material, a cheap and readily available base catalyst

  报道了硫醇与手性 β-三氟甲基-α,β-不饱和N-酰化恶唑烷-2-酮的碱催化非对映发散硫杂-迈克尔加成反应。通过调整碱催化剂（i -Pr 2 NEt、DABCO 或 P 2 - t -Bu），以良好的收率和高非对映选择性合成了一系列手性硫杂-迈克尔加合物。根据实验结果提出了一种合理的机制。这项工作是对现有方法的补充，提供了一些优点，例如，使用易于合成的手性起始材料、廉价且易于获得的碱催化剂、以及简单实用的操作来实现可切换的非对映选择性，使得能够在有机合成中进行合成应用。