8-Jod-naphthalin-carbonsaeure-(1)-chlorid | 32141-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-Jod-naphthalin-carbonsaeure-(1)-chlorid
• 英文别名: 8-Iodonaphthalene-1-carbonyl chloride
• CAS: 32141-11-0
• 化学式: C₁₁H₆ClIO
• 分子量: 316.526
• InChiKey: VTSAXFRCPZUNGI-UHFFFAOYSA-N

物化性质

• 沸点：
  383.7±15.0 °C(Predicted)
• 密度：
  1.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-Jod-naphthalin-carbonsaeure-(1)-chlorid 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 sodium hydride 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 69.0h， 生成 8-[4-[(E)-2-carboxyethenyl]phenyl]naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Toward Covalently Linked Organic Networks:  Model Studies and Connector Syntheses

  摘要：

  A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an alpha-truxillate-type cyclobutane photodimer in quantitative yield, Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of(pseudo)centrosymmetric attachment to polyvalent hubs, This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.

  DOI：

  10.1021/jo9714167
• 作为产物：
  描述：

  8-碘-1-萘酸 在 氯化亚砜 作用下， 生成 8-Jod-naphthalin-carbonsaeure-(1)-chlorid
  参考文献：
  名称：

  Staab,H.A. et al., Chemische Berichte, 1971, vol. 104, p. 1182 - 1190

  摘要：

  DOI：

文献信息

• Hellwinkel, Dieter; Bohnet, Siegbert, Chemische Berichte, 1987, vol. 120, p. 1151 - 1174
  作者：Hellwinkel, Dieter、Bohnet, Siegbert

  DOI：——

  日期：——
• Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process
  作者：Audrey-Anne Guilbault、Benoit Basdevant、Vincent Wanie、Claude Y. Legault

  DOI：10.1021/jo302393u

  日期：2012.12.21

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.
• Staab,H.A. et al., Chemische Berichte, 1971, vol. 104, p. 1182 - 1190
  作者：Staab,H.A. et al.

  DOI：——

  日期：——
• HELLWINKEL D.; BOHNET S., CHEM. BER., 120,(1987) N 7, 1151-1173
  作者：HELLWINKEL D.、 BOHNET S.

  DOI：——

  日期：——
• Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents
  作者：Jenny L. Wiley、Valerie J. Smith、Jianhong Chen、Billy R. Martin、John W. Huffman

  DOI：10.1016/j.bmc.2012.01.038

  日期：2012.3

  To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl) indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl) indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity. (C) 2012 Elsevier Ltd. All rights reserved.