(S)-N-(1-iso-propyl-2-hydroxyethyl)benzoylformamide | 113336-47-3

• 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: (S)-N-(1-iso-propyl-2-hydroxyethyl)benzoylformamide
• 英文别名: N-(1-hydroxymethyl-2-methylpropyl)benzoylformamide；N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-2-oxo-2-phenylacetamide
• CAS: 113336-47-3
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: NGLYFCURHPECAX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-iso-propyl-2-hydroxyethyl)benzoylformamide 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-((S)-1-Chloromethyl-2-methyl-propyl)-2-oxo-2-phenyl-acetamide
  参考文献：
  名称：

  Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes

  摘要：

  Starting either from benzoylformic acid or ethyl oxamate and enantiopure beta-amino alcohols, several chiral alpha-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.038
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 L-缬氨醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以19%的产率得到(S)-N-(1-iso-propyl-2-hydroxyethyl)benzoylformamide
  参考文献：
  名称：

  Kashima, Choji; Harada, Kazuo; Omote, Yoshimori, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1495 - 1500

  摘要：

  DOI：

文献信息

• Diastereoselective reduction and carboncarbon bond formation of α-keto esters/amides with SmI2
  作者：Shin-ichi Fukuzawa、Manabu Miura、Hiroshi Matsuzawa

  DOI：10.1016/s0040-4039(01)00676-1

  日期：2001.6

  The stereoselective reduction of alpha -keto esters/alpha -keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding alpha -hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the alpha -keto ester/amide proceeded smoothly with high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• KASHIMA, CHOJI;HARADA, KAZUO;OMOTE, YOSHIMORI, J. CHEM. SOC. PERKIN TRANS.,(1987) N 7, 1495-1499
  作者：KASHIMA, CHOJI、HARADA, KAZUO、OMOTE, YOSHIMORI

  DOI：——

  日期：——