(1S,2R,3R,4R)-3-carboxy-2-methoxycarbonylbicyclo(2.2.1)heptane | 125226-86-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,3R,4R)-3-carboxy-2-methoxycarbonylbicyclo(2.2.1)heptane
• 英文别名: (1S,2S,3R,4R)-2-(Methoxycarbonyl)bicyclo<2.2.1>heptane-3-carboxylic Acid；(1S,2R,3R,4R)-3-carboxy-2-methoxycarbonylbicyclo<2.2.1>heptane；(1S,2R,3R,4R)-2-methoxycarbonyl-3-carboxybicyclo[2.2.1]heptane；(1R,2R,3R,4S)-3-methoxycarbonylbicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 125226-86-0
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: AIMKQBORRFFXGP-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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,2R,3R,4R)-3-carboxy-2-methoxycarbonylbicyclo(2.2.1)heptane 在 lithium aluminium tetrahydride 、 草酰氯 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-Bromo-N-((1R,2R,3R,4S)-3-formyl-bicyclo[2.2.1]hept-2-ylmethyl)-benzenesulfonamide
  参考文献：
  名称：

  有效血栓素A 2 /前列腺素内过氧化物受体拮抗剂的合成。

  摘要：

  报道了新的和最有效的血栓烷A 2 /前列腺素内过氧化物拮抗剂的设计。

  DOI：

  10.1016/s0040-4039(01)80410-x
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 (1S,2R,3R,4R)-3-carboxy-2-methoxycarbonylbicyclo(2.2.1)heptane
  参考文献：
  名称：

  Highly effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptanedicarboxylic acid

  摘要：

  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.

  DOI：

  10.1021/jo00013a009

文献信息

• A versatile and highly stereocontrolled synthetic approach to homochiral polyfunctional norbornene and norbornane derivatives
  作者：Ramon Casas、Javier Ibarzo、José M. Jiménez、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(00)80174-3

  日期：1993.4

  chiral precursor. The target molecules include pairs of enantiomers and their configuration has mainly been assured by controlling the facial and the endo/exo diastereoselectivity in the Diels-Alder reactions of chiral cyclic or acyclic dienophiles. Some of the products obtained are key intermediates in the synthesis of biologically active compounds.

  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。
• Enantioselective production of homochiral (+)-(1R,2S,3S,4S)- and (−)-(1S,2R,3R,4R)-bicyclo(2.2.1)heptane-2,3-dicarboxylic acid, 2-methyl esters. Formal synthesis of the TXA2 antagonist S-1452.
  作者：Ramon Casas、Rosa M. Oituõ

  DOI：10.1016/s0957-4166(00)82106-0

  日期：1992.9

  Both enantiomers of the title half ester have been synthesized from -mannitol as single chiral precursor. The -enantiomer is the key intermediate in the synthesis of the TXA2 antagonistic drug S-1452.

  标题半酯的两种对映体均由-甘露醇合成为单一手性前体。所述对映体是在TXA的合成中的关键中间体2拮抗药物S-1452。
• Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives
  作者：Satomi Niwayama、Hanjoung Cho、Masoud Zabet-Moghaddam、Bruce R. Whittlesey

  DOI：10.1021/jo100564e

  日期：2010.6.4

  High exo-facial selectivity was observed in the selective monohydrolysis of a series of near-symmetric diesters that possess an exo-ester group and an endo-ester group attached on a norbornane or norbornene skeleton. The selectivities were found to be clear-cut, although the reaction center in these reactions is one covalent bond distant from the norbornane or norbornene ring, where the difference of the environment between the exo face and endo face is therefore expected to be negligible. The effect of the co-solvent we studied earlier for the selective monohydrolysis reaction was also confirmed and contributed to improvement of the yields of the half-esters.
• 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：——
• Mono esters of dicarboxylic acids, their preparation and use
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD.

  公开号：EP0373949B1

  公开（公告）日：1993-08-25