(1S,2S,3S,4R)-2-(Methoxycarbonyl)bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid | 116404-46-7

• 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: (1S,2S,3S,4R)-2-(Methoxycarbonyl)bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid
• 英文别名: (1S,2S,3S,4R)-3-carboxy-2-methoxycarbonylbicyclo<2.2.1>hept-5-ene；(1S,2S,3S,4R)-3-carboxy-2-methoxycarbonylbicyclo[2.2.1]hept-5-ene；(1R,2S,3S,4S)-3-methoxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS: 116404-46-7
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: JYZKYCYHXBQTCY-YWIQKCBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4R)-2-(Methoxycarbonyl)bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid 在 sodium azide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 (1S,2S,3S,4R)-3-carbobenzoxyamino-2-carbomethoxybicyclo<2.2.1>hept-5-ene
  参考文献：
  名称：

  口服活性血栓烷A2受体拮抗剂S-1452的代谢产物的合成。

  摘要：

  描述了口服活性血栓烷A2（TXA2）受体拮抗剂S-1452的16种代谢产物的合成。光学活性中间体16的双环[2.2.1]庚烷骨架的C-5或C-6区域选择性羟基化的方法是，先使用9-硼环[3.3.1]壬烷，然后加入H2O2或间氯过苯甲酸（m CPBA），然后再加入LiAlH4，分别得到羟基化产物17a或17b。修饰17a和17b的C-2取代基得到S-1452的八个代谢物。通过使用类似的反应顺序合成了八种非羟基化代谢物。

  DOI：

  10.1248/cpb.39.2842
• 作为产物：
  描述：

  (1S,2S,3S,4R)-3-<(1S)-epoxyethyl>-2-methoxycarbonylbicyclo<2.2.1>hex-5-ene 在 sodium periodate 、 重铬酸吡啶 、 高氯酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.25h， 生成 (1S,2S,3S,4R)-2-(Methoxycarbonyl)bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid
  参考文献：
  名称：

  一种多用途且高度立体控制的合成方法，用于制备手性多官能降冰片烯和降冰片烷衍生物

  摘要：

  已经从D-甘露醇合成了几种标题化合物作为独特的手性前体。目标分子包括成对的对映体，并且主要通过控制手性环状或无环亲二烯体的Diels-Alder反应中的面部和内/外非对映选择性来确保其构型。获得的某些产物是生物活性化合物合成中的关键中间体。

  DOI：

  10.1016/s0957-4166(00)80174-3

文献信息

• Structural requirements in the enzymic optical resolution of bicyclic esters using pig liver esterase
  作者：A.J.H Klunder、F.J.C van Gastel、B Zwanenburg

  DOI：10.1016/0040-4039(88)85263-8

  日期：——

  The PLE-catalyzed hydrolysis of bicyclic mono- and diesters 4–15 have been studied. Structural features such as bridge size and relative configuration of the ester functions have found to be essential for effective hydrolysis. A high degree of stereo- and enantioselectivity was observed for -bicyclo-12.2.1]heptane-2,3-diesters 4, 5 and 6.

  已经研究了PLE催化的双环单酯和双酯4-15的水解。已经发现结构特征例如桥的大小和酯官能团的相对构型对于有效水解是必不可少的。观察到高度的立体和对映体选择性-二环-12.2.1]庚烷-2,3-二酯4，5和6。
• Norbornene-based ring-opening polymerization polymer, product of hydrogenation of norbornene-based ring-opening polymerization polymer, and processes for producing these
  申请人：Taguchi Kazunori

  公开号：US20050148746A1

  公开（公告）日：2005-07-07

  A norbornene ring-opened polymer which in the molecule has repeating units represented by the formula (1): wherein R 1 represents Q, R 2 represents Q or C(═O)R 5 , R 3 represents Q or C(═O)R 6 , and R 4 represents Q or X—C(═O)R 7 (wherein Q represents hydrogen, a C 1-10 hydrocarbon group, etc.; R 5 , R 6 and R 7 each represents hydroxyl, C 1-10 alkoxyl, etc., provided that R 6 and R 7 may be bonded to each other to constitute oxygen, NH, etc.; X represents methylene, etc., provided that when R 2 is Q, then R 3 is C(═O)R 6 and R 4 is X—C(═O)R 7 and that when R 4 is Q, then R 2 is C(═O)R 5 , R 3 is C(═O)R 6 , and the configuration of R 2 and R 3 is trans, and m is 0 or 1), the polymer having a weight-average molecular weight as determined by gel permeation chromatography of 1,000 to 1,000,000. Also provided is a hydrogenation product of the norbornene ring-opened polymer. The norbornene ring-opened polymer and the hydrogenation product are excellent in heat resistance, electrical properties, etc.

  分子中具有由公式（1）表示的重复单元的去氢萘环开环聚合物：其中R1表示Q，R2表示Q或C（═O）R5，R3表示Q或C（═O）R6，R4表示Q或X—C（═O）R7（其中Q表示氢，C1-10烃基等；R5，R6和R7分别表示羟基，C1-10烷氧基等，但是当R6和R7结合形成氧，NH等时除外；X表示亚甲基等，但是当R2为Q时，R3为C（═O）R6，R4为X—C（═O）R7，当R4为Q时，R2为C（═O）R5，R3为C（═O）R6，并且R2和R3的构型为反式，m为0或1），该聚合物的重均分子量由凝胶渗透色谱法确定为1,000至1,000,000。还提供了去氢萘环开环聚合物的氢化产物。去氢萘环开环聚合物和氢化产物在耐热性，电学性能等方面表现出色。
• Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid
  作者：Mitsuaki Ohtani、Takaharu Matsuura、Fumihiko Watanabe、Masayuki Narisada

  DOI：10.1021/jo00013a009

  日期：1991.6

  An effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptane-2,3-dicarboxylic acid was developed by enantioselective fission of sigma-symmetrical cyclic anhydrides with chiral mandelic acid derivatives, followed by deprotection of the mandelate moiety, crystallization, and further modification. These half-esters are very attractive chiral building blocks for numerous natural products, and this new method makes possible their synthesis via common intermediates with high optical purity.
• [4 + 2] Cycloaddition Reactions Catalyzed by a Chiral Oxazaborolidinium Cation. Reaction Rates and Diastereo-, Regio-, and Enantioselectivity Depend on Whether Both Bonds Are Formed Simultaneously
  作者：Santanu Mukherjee、E. J. Corey

  DOI：10.1021/ol100032u

  日期：2010.3.5

  The reaction rates and products in enantioselective Diels-Alder reactions with a range of dienophiles correlate with the expected degree of concertedness of bond formation in the transition state.
• OHTANI, MITSUAKI;MATSUURA, TAKAHARU;WATANABE, FUMIHIKO;NARISADA, MASAYUKI, J. ORG. CHEM., 56,(1991) N3, C. 4120-4123
  作者：OHTANI, MITSUAKI、MATSUURA, TAKAHARU、WATANABE, FUMIHIKO、NARISADA, MASAYUKI

  DOI：——

  日期：——