(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid | 70190-87-3

• 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: (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid
• 英文别名: (1S,2S,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid；norbornene-5,6-dicarboxylic acid；5-Norbornene-2,3-dicarboxylic acid, (1R,2S,3S,4S)-
• CAS: 70190-87-3
• 化学式: C₉H₁₀O₄
• mdl: MFCD12026879
• 分子量: 182.176
• InChiKey: NIDNOXCRFUCAKQ-VZFHVOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 在 碘 、 碳酸氢钠 、 potassium iodide 作用下， 反应 0.83h， 生成 (+/-)-(1S*,2R*,4S*,5S*,6R*,9S*)-9-Iodo-7-oxo-8-oxatricyclo<4.2.1.0^2,6>nonane 5-carboxylic acid
  参考文献：
  名称：

  具有降冰片烷骨架的γ-氨基酸衍生的新型二肽的合成与构象

  摘要：

  从降冰片烯二羧酸 5 合成了具有降冰片烷骨架的对映异构纯 γ-氨基酸 9。对衍生自该氨基酸的受保护二肽 10 的 NOE 研究和 AM1 计算表明，肽主链的构象由下式确定两个亚基之间的分子内氢键。

  DOI：

  10.1055/s-1999-3115
• 作为产物：
  描述：

  bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以46%的产率得到(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid
  参考文献：
  名称：

  Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts

  摘要：

  Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)(2)-, Zn(OTf)(2)-, and Cu(OTf)(2)-catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%. Surprisingly, a non-C-2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00323-6

文献信息

• Asymmetric Synthesis of a New Salen Type-titanium Complex as the Catalyst for Asymmetric Trimethylsilylcyanation of Aldehydes
  作者：Zheng-Chang Lin、Chinpiao Chen

  DOI：10.1002/jccs.201000101

  日期：2010.8

  This work describes the asymmetric synthesis of a new salen‐type ligand via a Diels‐Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destroy this rigidity, and the eanatioselectivity was thereby increased to 85%ee.

  这项工作描述了通过Diels-Alder反应和Curtius重排的新Salen型配体的不对称合成。具有降冰片烷骨架的配体用于醛的三甲基甲硅烷基氰化中，但对映选择性为55％ee。切割去甲硼烷骨架以破坏该刚性，从而将选择性选择性提高至85％ee。
• Receptor
  申请人：Nelissen Hubertus Franciscus Martinus

  公开号：US20080221218A1

  公开（公告）日：2008-09-11

  The present invention relates to synthetic receptors, products and methods which are useful in relation to the binding of phosphates for example in water purification and renal dialysis systems.

  本发明涉及合成受体、产品和方法，这些受体、产品和方法在与磷酸盐的结合有关的应用中非常有用，例如在水净化和肾透析系统中。
• Synthesis of a Novel Enantiomerically Pure Chlorin as a Potential Subunit for an Artificial Photosynthetic Reaction Center
  作者：Wolfgang Schmidt、Franz-Peter Montforts

  DOI：10.1055/s-1997-942

  日期：1997.8

  The total synthesis of an enantiomerically pure chlorin with two different functional groups as a potential subunit for the construction of artificial photosynthetic reaction centers was achieved.

  实现了具有两个不同官能团的对映体纯二氢卟酚作为构建人工光合反应中心的潜在亚基的全合成。
• The synthesis of a 3-diazobicyclo[2.2.1]Heptan-2-one inhibitor of thromboxane a2 synthetase
  作者：Jerry L. Adams、Brian W. Metcalf

  DOI：10.1016/s0040-4039(01)80062-9

  日期：1984.1

  The synthesis of a PGH2 analog 5-(2(Z), 6-(1E)-3-diazo-5-(7-hydroxy-2-heptenyl)-6-(3-hydroxy-1-octenyl)bicyclo[2.2.1]heptan-2-one 2 is described.

  PGH 2类似物5- （2（Z），6- （1E）-3-重氮-5-（7-羟基-2-庚烯基）-6-（3-羟基-1-辛烯基）双环[ [2.2.1]庚烷-2-酮2被描述。
• RESIST UNDERLAYER FILM-FORMING COMPOSITION, PRODUCTION METHOD OF SEMICONDUCTOR DEVICE USING THE SAME, AND ADDITIVE FOR RESIST UNDERLAYER FILM-FORMING COMPOSITION
  申请人：Nakajima Makoto

  公开号：US20100210765A1

  公开（公告）日：2010-08-19

  There is provided a composition for forming a resist underlayer film that the adhesion with a resist applied on the resist underlayer film is enhanced and the collapse of a resist pattern is suppressed. A resist underlayer film-forming composition for lithography comprising: a polymer having silicon atoms in the backbone; a compound of a polycyclic structure; and an organic solvent, wherein the compound of a polycyclic structure has at least two carboxyl groups as substituents; the two carboxyl groups are individually bonded to two carbon atoms adjacent to each other forming the polycyclic structure; and the two carboxyl groups both have an endo configuration or an exo configuration, or have a cis configuration.

  提供了一种用于形成抗蚀底层膜的组合物，其增强了与施加在抗蚀底层膜上的抗蚀剂的粘附性并抑制了抗蚀图案的崩溃。一种用于光刻的抗蚀底层膜形成组合物，包括：具有硅原子的聚合物骨架；多环结构的化合物；和有机溶剂，其中，多环结构的化合物具有至少两个羧基作为取代基；这两个羧基分别与相邻的两个碳原子形成多环结构的键合；这两个羧基都具有内向构型或外向构型，或具有顺式构型。