(R)-2-allyl-2-amino-4-(4-bromophenyl)pent-4-enoic acid tert-butyl ester | 1173893-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-allyl-2-amino-4-(4-bromophenyl)pent-4-enoic acid tert-butyl ester
• 英文别名: tert-butyl (2R)-2-amino-4-(4-bromophenyl)-2-prop-2-enylpent-4-enoate
• CAS: 1173893-40-7
• 化学式: C₁₈H₂₄BrNO₂
• 分子量: 366.298
• InChiKey: XAXLKLOYMQTYCS-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (R)-2-allyl-2-amino-4-(4-bromophenyl)pent-4-enoic acid tert-butyl ester 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以87%的产率得到(R)-2-allyl-4-(4-bromophenyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  A stereoselective and scalable synthesis of a conformationally constrained S1P1 agonist

  摘要：

  A scalable and enantioselective synthesis of a potent SIP1 agonist containing two stereogenic centers oil a cyclopentane ring is described. Control of the absolute chirality of an amino alcohol precursor, generated via a robust phase-transfer catalyzed alkylation protocol, allows for Substrate directed hydrogenation to install the second stereogenic center providing access to gram-quantities of compound 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.099
• 作为产物：
  描述：

  2-{[1-(4-chlorophenyl)methylidene]amino}pent-4-enoic acid tert-butyl ester 、 1-bromo-4-(3-bromoprop-1-en-2-yl)benzene 在 (11bS,11b’S)-2,6-bis(3,4,5-trifluorophenyl)-3,3’,5,5’-tetrahydro-4,4’-spirobi[dinaphtho[2,1-c:1’,2’-e]azepin]-4-ium bromide 、 caesium hydroxide monohydrate 、 柠檬酸 作用下， 以 甲苯 、 四氢呋喃 、 水 为溶剂， 反应 25.0h， 以62.3%的产率得到(R)-2-allyl-2-amino-4-(4-bromophenyl)pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  A stereoselective and scalable synthesis of a conformationally constrained S1P1 agonist

  摘要：

  A scalable and enantioselective synthesis of a potent SIP1 agonist containing two stereogenic centers oil a cyclopentane ring is described. Control of the absolute chirality of an amino alcohol precursor, generated via a robust phase-transfer catalyzed alkylation protocol, allows for Substrate directed hydrogenation to install the second stereogenic center providing access to gram-quantities of compound 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.099

文献信息

• A stereoselective and scalable synthesis of a conformationally constrained S1P1 agonist
  作者：Shannon R. Fix-Stenzel、Martin E. Hayes、Xiaolei Zhang、Grier A. Wallace、Pintipa Grongsaard、Lisa M. Schaffter、Steven M. Hannick、Thaddeus S. Franczyk、Robert H. Stoffel、Kevin P. Cusack

  DOI：10.1016/j.tetlet.2009.04.099

  日期：2009.7

  A scalable and enantioselective synthesis of a potent SIP1 agonist containing two stereogenic centers oil a cyclopentane ring is described. Control of the absolute chirality of an amino alcohol precursor, generated via a robust phase-transfer catalyzed alkylation protocol, allows for Substrate directed hydrogenation to install the second stereogenic center providing access to gram-quantities of compound 2. (C) 2009 Elsevier Ltd. All rights reserved.