3-(R)-3-[2-(R)-2-methoxy-2-phenyl-2-trifluoromethyl]acetoxybutyric acid methyl ester | 76904-87-5

• 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: 3-(R)-3-[2-(R)-2-methoxy-2-phenyl-2-trifluoromethyl]acetoxybutyric acid methyl ester
• 英文别名: methyl (3R)-3-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxybutanoate
• CAS: 76904-87-5
• 化学式: C₁₅H₁₇F₃O₅
• 分子量: 334.292
• InChiKey: ITUWCTKDQJDLPN-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (R)-3-羟基丁酸甲酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(R)-3-[2-(R)-2-methoxy-2-phenyl-2-trifluoromethyl]acetoxybutyric acid methyl ester
  参考文献：
  名称：

  Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones

  摘要：

  Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.

  DOI：

  10.1016/s0040-4020(01)86300-6

文献信息

• ASYMMETRIC HYDROGENATION OF 3-OXO CARBOXYLATES USING BINAP-RUTHENIUM COMPLEXES: (R)-(−)-METHYL 3-HYDROXYBUTANOATE
  作者：Kitamura, Masato、Tokunaga, Makoto、Ohkuma, Takeshi、Noyori, Ryoji

  DOI：10.15227/orgsyn.071.0001

  日期：——
• Bellisosides A–F, six novel acylated triterpenoid saponins from Bellis perennis (compositae)
  作者：Wei Li、Yoshihisa Asada、Kazuo Koike、Tamotsu Nikaido、Tsutomu Furuya、Takafumi Yoshikawa

  DOI：10.1016/j.tet.2005.01.026

  日期：2005.3

  Six new acylated triterpenoid saponins, bellisosides A-F (1-6), were isolated from the roots of Bellis perennis (Compositae) together with a known saponin, bellissaponin BS2 (7). These saponins which bear polygalacic acid as sapogenin, are bisdesmosidic glycosides. The structures were elucidated on the basis of chemical and physicochemical evidence. The cytotoxic activities of 1-7 against HL-60 human promyelocytic leukemia cells are also reported. (c) 2005 Elsevier Ltd. All rights reserved.