cis-4-benzoylamino-2-cyclopentenecarboxylic acid methyl ester

• 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: cis-4-benzoylamino-2-cyclopentenecarboxylic acid methyl ester
• 英文别名: methyl (1S,4R)-4-benzamidocyclopent-2-ene-1-carboxylate
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: XDQLOYCVOXFWRC-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-4-benzoylamino-2-cyclopentenecarboxylic acid methyl ester 在 barium dihydroxide 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 水 、 双氧水 作用下， 以 吡啶 为溶剂， 生成 (+/-)-(1α,3α,4β)-3-amino-4-hydroxycyclopentanemethanol
  参考文献：
  名称：

  （±）-3'-deoxyaraaristeromycin通过令人惊讶的重排

  摘要：

  已经发现（+）-3β-乙酰氧基-4α-苯甲酰胺基-1α-环戊烷乙酸甲酯（5）用6N盐酸水解得到胺，其中C-3处的构型已经被反转。通过遵循以下标准的腺嘌呤形成过程，将胺转化为（+）-3'-deoxyaraaristeromycin（8），可以得出这一结论：（i）与5-氨基-4,6-dichlocopyrimidine反应，（ii）与二乙氧基乙酸甲酯，和（iii）氨解。使用5的碱性水解条件可产生预期的（+）3'脱氧阿霉素（7）。

  DOI：

  10.1016/s0040-4039(00)73876-7
• 作为产物：
  描述：

  2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 硫酸 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 生成 cis-4-benzoylamino-2-cyclopentenecarboxylic acid methyl ester
  参考文献：
  名称：

  Development of the biocatalytic resolution of 2-azabicyclo[2.2.1]hept-5-en-3-one as an entry to single-enantiomer carbocyclic nucleosides

  摘要：

  For the resolution of the bicyclic lactam 2-azabicyclo[2.2.1]hept-5-en-3-one, efficient whole cell biocatalysts have been identified and from these, enzymes (lactamases) have been isolated. While the two enzymes obtained act on different enantiomers of the lactam, either can be used in scaleable processes to obtain synthons for carbocyclic nucleosides having the natural configuration.

  DOI：

  10.1016/s0957-4166(00)80218-9

文献信息

• Metal-Catalyzed Reactions between 2-Azabicyclo[2.2.1]hept-5-en-3-ones and Arylboronic Acids
  作者：Takumi Abe、Hiroyuki Takeda、Yumi Takahashi、Yoshihisa Miwa、Koji Yamada、Minoru Ishikura

  DOI：10.1002/ejoc.201000135

  日期：2010.6

  Cu- and Rh-catalyzed coupling reactions of 2-azabicyclo[2.2.1]hept-5-en-3-ones (1) with arylboronic acids were successful carried out under microwave irradiation conditions and yielded N-aryl and C-aryl derivatives of 1, respectively.

  Cu-和Rh-催化的2-氮杂双环[2.2.1]hept-5-en-3-ones (1)与芳基硼酸的偶联反应在微波辐射条件下成功进行，得到N-芳基和C-芳基衍生物分别为 1。
• Rhodium-Catalyzed Arylation of 2-Azabicyclo[2.2.1]hept-5-en-3-one with Arylboronic Acids under Microwave Irradiation
  作者：Minoru Ishikura、Takumi Abe、Hiroyuki Takeda、Yumi Takahashi、Yoshihisa Miwa、Koji Yamada

  DOI：10.3987/com-08-11483

  日期：——

  - Rhodium-catalyzed arylation of 2-azabicyclo[2.2.1]hept-5-en-3-one was successfully performed by applying microwave irradiation.

  - 2-azabicyclo[2.2.1]hept-5-en-3-one 的铑催化芳基化通过微波辐射成功进行。
• Unexpected stereoselectivity in the cis dihydroxylation of some 2-cyclopentene-1-carboxamides
  作者：Christopher F Palmer、Raymond McCague、Graham Ruecroft、Sean Savage、Stephen J.C Taylor、Christel Ries

  DOI：10.1016/0040-4039(96)00887-8

  日期：1996.6

  While 4-substituted-2-cyclopentene-1-carboxylate esters gave no facial selectivity in the cis dihydroxylation of the olefin function with osmium tetroxide/N-methylmorpholine-N-oxide, the corresponding carboxamides unexpectedly gave high diastereoselectivity for the isomer useful for carbocyclic ribofuranosyl nucleosides.

  尽管4-取代的2-环戊烯-1-羧酸酯在四官能os / N-甲基吗啉-N-氧化物的烯烃官能团的顺式二羟基化反应中没有面部选择性，但相应的羧酰胺出乎意料地为可用于碳环的异构体提供了高非对映选择性核呋喃糖基核苷。
• Synthesis and Antiviral Activity of the Carbocyclic Analogue of the Highly Potent and Selective Anti-VZV Bicyclo Furano Pyrimidines
  作者：Marco D. Migliore、Nicola Zonta、Christopher McGuigan、Geoffrey Henson、Graciela Andrei、Robert Snoeck、Jan Balzarini

  DOI：10.1021/jm070357e

  日期：2007.12.27

  chemically more stable than the furano lead, but it was shown to be significantly less antivirally active than its parent nucleoside analogue. It was noted to have a 10-fold lower inhibitory activity against the VZV-encoded thymidine kinase. This reduction of activity may be attributed to the different conformation of the sugar and base, as predicted by computational studies and supported by NMR studies

  碳环核苷类似物是分解代谢稳定的，因为它们对嘧啶核苷磷酸化酶的磷酸裂解具有抗性。以碳环2'-脱氧尿苷为起始原料，合成了高效，高选择性的VZV双环核苷类似物（BCNA）6-戊基苯基呋喃[2,3-d]嘧啶-2'-脱氧核糖的碳环类似物（C-BCNA）。 。发现C-BCNA在化学上比呋喃诺铅更稳定，但已证明其抗病毒活性远低于其母体核苷类似物。注意到对VZV编码的胸苷激酶的抑制活性降低了10倍。活性的这种降低可以归因于糖和碱的不同构象，如通过计算研究预测并得到NMR研究支持。然而，
• Improved procedures for the preparation of (+) - (1R, 2S, 4R)-4-amino-2-hydroxy-1-hydroxymethyl cyclopentane
  作者：Brian L. Bray、Simon C. Dolan、Bernard Halter、J.William Lackey、Mark B. Schilling、David J. Tapolczay

  DOI：10.1016/0040-4039(95)00764-4

  日期：1995.6

  Two methods for the stereospecific synthesis of the title compound are described. These short and efficient syntheses provide rapid access to this key intermediate in the construction of 2′-Deoxy Carbocyclic Nucleosides.

  描述了两种立体定向合成标题化合物的方法。这些短而有效的合成为构建2'-脱氧碳环核苷中的关键中间体提供了快速途径。