(R)-methyl 4-(bis(tert-butoxycarbonyl)amino)cyclopent-1-enecarboxylate | 1416177-64-4

• 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)-methyl 4-(bis(tert-butoxycarbonyl)amino)cyclopent-1-enecarboxylate
• 英文别名: methyl (4R)-4-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]cyclopentene-1-carboxylate
• CAS: 1416177-64-4
• 化学式: C₁₇H₂₇NO₆
• 分子量: 341.404
• InChiKey: FKYPWJBKKIRESE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-methyl 4-(bis(tert-butoxycarbonyl)amino)cyclopent-1-enecarboxylate 在 三异丙基亚磷酸酯 、 palladium diacetate 、 臭氧 、 sodium sulfate 、 对甲苯磺酰肼 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 生成 methyl (2R,3aR,6aR)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-2,3,4,5,6,6a-hexahydro-1H-pentalene-3a-carboxylate
  参考文献：
  名称：

  Novel 2-aminooctahydrocyclopentalene-3a-carboxamides as potent CCR2 antagonists

  摘要：

  Novel CCR2 antagonists with a novel 2-aminooctahydrocyclopentalene-3a-carboxamide scaffold were designed. SAR studies led to a series of potent compounds. For example, compound 51 had a good PK profile in both dog and monkey, and exhibited excellent efficacy when dosed orally in an inflammation model in hCCR2 KI mice. In addition, an asymmetric synthesis to the core structures was developed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.069
• 作为产物：
  描述：

  (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 4-二甲氨基吡啶 、 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 90.5h， 生成 (R)-methyl 4-(bis(tert-butoxycarbonyl)amino)cyclopent-1-enecarboxylate
  参考文献：
  名称：

  Chiral aminocyclopentene-based cycloaddition strategies to bicyclic [3.3.0] rings

  摘要：

  Two cycloaddition methods were applied to chiral protected aminocyclopentenes 2 and 9 and provided novel bicyclic products 3 and 4 in good yields. The explanation for the observed stereochemistry was based on the sterically encumbered beta-face forcing the cycloadditions to occur on the alpha-face of the cyclopentene ring. The stereochemistry of 4 was confirmed by X-ray of the fumarate salt 10 and showed the trans-relationship between the newly formed ring and the chiral -NHBoc group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.014

文献信息

• Regio- and Stereoselective Synthesis of Functionalized Cyclopentene Derivatives via Mizoroki–Heck Reactions
  作者：Alexander Wetzel、Joakim Bergman、Peter Brandt、Mats Larhed、Jonas Brånalt

  DOI：10.1021/acs.orglett.7b00325

  日期：2017.4.7

  Mizoroki–Heck alkenylations and arylations of protected aminocyclopentenes, prepared in a few steps from Vince lactam, afforded functionalized cyclopentenes in high yields and stereoselectivities. DFT calculations were performed to rationalize the high diastereoselectivities. Functionalized cyclopentene products were transformed into valuable chiral building blocks, such as cyclic γ-amino acids and carbocyclic

  Pd（0）催化的从Vince内酰胺制备的受保护的氨基环戊烯的Mizoroki-Heck烯基化和芳基化（从文斯内酰胺制备）仅需几步即可提供高产率和立体选择性的官能化环戊烯。进行DFT计算以合理化高非对映选择性。功能化的环戊烯产物被转化为有价值的手性构件，例如环状γ-氨基酸和碳环核苷前体。
• Novel 2-aminooctahydrocyclopentalene-3a-carboxamides as potent CCR2 antagonists
  作者：Chaozhong Cai、Fu-An Kang、Cuifen Hou、John C. O’Neill、Evan Opas、Sandra McKenney、Dana Johnson、Zhihua Sui

  DOI：10.1016/j.bmcl.2012.10.069

  日期：2013.1

  Novel CCR2 antagonists with a novel 2-aminooctahydrocyclopentalene-3a-carboxamide scaffold were designed. SAR studies led to a series of potent compounds. For example, compound 51 had a good PK profile in both dog and monkey, and exhibited excellent efficacy when dosed orally in an inflammation model in hCCR2 KI mice. In addition, an asymmetric synthesis to the core structures was developed. (C) 2012 Elsevier Ltd. All rights reserved.
• Chiral aminocyclopentene-based cycloaddition strategies to bicyclic [3.3.0] rings
  作者：Chaozhong Cai、Fu-An Kang、Derek A. Beauchamp、Zhihua Sui、Ronald K. Russell、Christopher A. Teleha

  DOI：10.1016/j.tetasy.2013.04.014

  日期：2013.6

  Two cycloaddition methods were applied to chiral protected aminocyclopentenes 2 and 9 and provided novel bicyclic products 3 and 4 in good yields. The explanation for the observed stereochemistry was based on the sterically encumbered beta-face forcing the cycloadditions to occur on the alpha-face of the cyclopentene ring. The stereochemistry of 4 was confirmed by X-ray of the fumarate salt 10 and showed the trans-relationship between the newly formed ring and the chiral -NHBoc group. (C) 2013 Elsevier Ltd. All rights reserved.