1,2,3,4-tetrahydro-9-oxo-1,4-ethanonaphthalene-2,3-endo-dicarboxylic anhydride | 4428-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1,2,3,4-tetrahydro-9-oxo-1,4-ethanonaphthalene-2,3-endo-dicarboxylic anhydride
• 英文别名: 1,4-Ethano-2-oxo-1,2,3,4-tetrahydronaphthalene-9,10-endo-dicarboxylic anhydride；(+/-)-9-oxo-1,2,3,4-tetrahydro-1r,4c-ethano-naphthalene-2t,3t-dicarboxylic acid-anhydride；(+/-)-9-Oxo-1,2,3,4-tetrahydro-1r,4c-aethano-naphthalin-2t,3t-dicarbonsaeure-anhydrid；(1S,8R,9R,13S)-11-oxatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-10,12,14-trione
• CAS: 4428-22-2；77286-28-3；77286-30-7；106760-62-7
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: NCIFOAQKJBQKSO-IXLVHKGHSA-N

物化性质

• 沸点：
  499.3±45.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-9-oxo-1,4-ethanonaphthalene-2,3-endo-dicarboxylic anhydride 在 palladium on activated charcoal 水 、 氢气 、 间氯过氧苯甲酸 、 肼 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (1R,2S,3R,4S,8R,9S,10R,11S)-hexacyclo[9.6.2.02,10.03,9.04,8.012,17]nonadeca-12,14,16-triene
  参考文献：
  名称：

  The benzo- and azo(azoxy)-chromophors as π6/π2-components in photocycloaddition reactions

  摘要：

  DOI：

  10.1016/s0040-4039(00)84236-7
• 作为产物：
  描述：

  马来酸酐 、 2-萘酚 生成 1,2,3,4-tetrahydro-9-oxo-1,4-ethanonaphthalene-2,3-endo-dicarboxylic anhydride
  参考文献：
  名称：

  447.酮的吸收光谱。第四部分 羰基与βγ-双键之间光谱相互作用的空间要求

  摘要：

  DOI：

  10.1039/jr9560002302

文献信息

• Diels-Alder reaction—IX
  作者：Ken'ichi Takeda、S. Hagishita、M. Sugiura、K. Kitahonoki、I. Ban、S. Miyazaki、K. Kuriyama

  DOI：10.1016/s0040-4020(01)92973-4

  日期：1970.1

  The Diels-Alder reaction of 1,7-, 2,7-, 2,6-, 1,6-dihydroxynaphthalene and 6-bromo-2-naphthol with maleic anhydride was investigated. All of these 2-naphthol derivatives gave exo- and endo-adducts (II and III) except for the bromo-naphthol, from which only endo-adduct was obtained. The assignment of exo or endo configuration was based on lactone formation on NaBH4 reduction possible only from the exo

  研究了1,7-，2,7-，2,6-，1,6-二羟基萘和6-溴-2-萘酚与马来酸酐的Diels-Alder反应。所有这些2-萘酚衍生物的给外-和内切-adducts（II和III），除了溴萘酚，其中只有内切得到-adduct。的分配外切或内切配置是基于上的NaBH内酯形成4减少可能只从外异构体，NMR谱的比较，并且在一些情况下，偶极矩的测量。形成的加合物的外/内比率在很宽的范围内变化。
• 447. Absorption spectra of ketones. Part IV. The steric requirements for spectroscopic interaction between a carbonyl group and a βγ-double bond
  作者：R. C. Cookson、N. S. Wariyar

  DOI：10.1039/jr9560002302

  日期：——
• Srivastava, V.; Srivastava, A.; Verma, S. M., Polish Journal of Chemistry, 1992, vol. 66, # 3, p. 477 - 484
  作者：Srivastava, V.、Srivastava, A.、Verma, S. M.

  DOI：——

  日期：——
• Design, Synthesis, Resolution, Determination of Absolute Configuration, and Evaluation of a Chiral Naproxen Selector
  作者：William H. Pirkle、Yuelong Liu

  DOI：10.1021/jo00102a013

  日期：1994.11

  A rigid chiral selector intended to differentiate between the enantiomers of alpha-arylpropionic acids (profens) has been designed and synthesized. The pi-acidic, hydrogen bond donor, and pi-basic interaction sites deemed essential to chiral recognition are supported on a [2.2.2]bicyclooctane framework to form a cleft-like ''active site'' in which enantiodiscrimination occurs. The racemic selector has been resolved chromatographically and the absolute configurations of the enantiomers have been established by a combination of HPLC and NMR methods. Immobilized on silica, this selector affords a chiral stationary phase which shows appreciable levels of enantioselectivity toward the profens, members of an important group of nonsteroidal antiinflammatory drugs. Immobilization has been accomplished in two ways. The selector has been hydrosilylated with either dimethylchlorosilane or with polymethylhydrosiloxane. The former leads to a brush-type CSP whereas the latter leads to a polymeric CSP coated and bonded to the silica support. The polysiloxane-based phase exhibits higher enantioselectivity and shorter retention times than does its brush-type counterpart. A mechanistic hypothesis advanced to account for the enantiodiscrimination observed suggests that relatively simple changes in the structure of the selector might further improve its enantioselectivity.
• Takeda; Kitahonoki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 280,282
  作者：Takeda、Kitahonoki

  DOI：——

  日期：——