(1S)-(1-methoxycarbamoyl-3-phenylpropyl)carbamic acid benzyl ester | 602307-73-3

• 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: (1S)-(1-methoxycarbamoyl-3-phenylpropyl)carbamic acid benzyl ester
• 英文别名: benzyl (S)-(1-(methoxyamino)-1-oxo-4-phenylbutan-2-yl)carbamate；benzyl N-[(2S)-1-(methoxyamino)-1-oxo-4-phenylbutan-2-yl]carbamate
• CAS: 602307-73-3
• 化学式: C₁₉H₂₂N₂O₄
• 分子量: 342.395
• InChiKey: LLCCMGXGCUKUDH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-(1-methoxycarbamoyl-3-phenylpropyl)carbamic acid benzyl ester 在 三氟乙酸 、 [双(三氟乙酰氧基)碘]苯 、 水 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到(3S)-(1-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of optically active α-aminobenzolactam via an oxidative–cyclization reaction

  摘要：

  A convergent pathway for the asymmetric synthesis of (-)-alpha-aminobenzolactam I is described. For the first time, the key intermediate N-methoxybenzolactam 8 was prepared from L-homophenylalanine ethyl ester hydrochloride (LHPE.HCl) 5 by employing an oxidative cyclization in the presence of trifluoroacetic acid (TFA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00408-7
• 作为产物：
  描述：

  氯甲酸苄酯 在 氢氧化钾 、 盐酸羟胺 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (1S)-(1-methoxycarbamoyl-3-phenylpropyl)carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of optically active α-aminobenzolactam via an oxidative–cyclization reaction

  摘要：

  A convergent pathway for the asymmetric synthesis of (-)-alpha-aminobenzolactam I is described. For the first time, the key intermediate N-methoxybenzolactam 8 was prepared from L-homophenylalanine ethyl ester hydrochloride (LHPE.HCl) 5 by employing an oxidative cyclization in the presence of trifluoroacetic acid (TFA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00408-7

文献信息

• Palladium(<scp>ii</scp>)-catalyzed asymmetric C–H carbonylation to diverse isoquinoline derivatives bearing all-carbon quaternary stereocenters
  作者：Yan Li、Xiu-Fen Cheng、Fan Fei、Tian-Rui Wu、Kang-Jie Bian、Xin Zhou、Xi-Sheng Wang

  DOI：10.1039/d0cc05219a

  日期：——

  Enantioselective synthesis of tetrahydroisoquinolines bearing an all-carbon quaternary stereogenic center, was achieved via asymmetric C–H activation with high enantioselectivities (up to 93% ee). Fair substrate tolerance was indicated throughout the scope investigation and no evident loss of enantioselectivity was exhibited in late-stage derivatization. This study provides incentives for the construction

  通过具有高对映选择性（高达93％ee）的不对称C–H活化，实现了带有全碳四级立体中心的四氢异喹啉的对映选择性合成。在整个范围的研究中均显示了良好的底物耐受性，并且在后期衍生化过程中未显示出明显的对映选择性损失。这项研究为构建各种手性异喹啉衍生物提供了动力，这些衍生物在药物，天然产品等中很普遍。
• Synthesis of optically active α-aminobenzolactam via an oxidative–cyclization reaction
  作者：Ching-Yao Chang、Teng-Kuei Yang

  DOI：10.1016/s0957-4166(03)00408-7

  日期：2003.7

  A convergent pathway for the asymmetric synthesis of (-)-alpha-aminobenzolactam I is described. For the first time, the key intermediate N-methoxybenzolactam 8 was prepared from L-homophenylalanine ethyl ester hydrochloride (LHPE.HCl) 5 by employing an oxidative cyclization in the presence of trifluoroacetic acid (TFA). (C) 2003 Elsevier Science Ltd. All rights reserved.