7,8-dihydro-5-oxonaphtho[2,3-d]-1,3-dioxole-6,6(5H)-dicarboxylic acid diethyl ester | 122951-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,8-dihydro-5-oxonaphtho[2,3-d]-1,3-dioxole-6,6(5H)-dicarboxylic acid diethyl ester
• 英文别名: diethyl 5-oxo-7,8-dihydrobenzo[f][1,3]benzodioxole-6,6-dicarboxylate
• CAS: 122951-01-3
• 化学式: C₁₇H₁₈O₇
• 分子量: 334.326
• InChiKey: PQOJAYVGDGUJEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 diethyl 2-[2-(6-iodo-1,3-benzodioxol-5-yl)ethyl]propanedioate 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-双(二苯基膦)丙烷 potassium carbonate 作用下， 以 xylene 为溶剂， 反应 24.0h， 以75%的产率得到7,8-dihydro-5-oxonaphtho[2,3-d]-1,3-dioxole-6,6(5H)-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Rh(I)-catalyzed CO gas-free carbonylative cyclization of organic halides with tethered nucleophiles using aldehydes as a substitute for carbon monoxide

  摘要：

  The CO gas-free carbonylative cyclization of organic halides, with tethered nitrogen, oxygen, and carbon nucleophiles, with aldehydes as a substitute for carbon monoxide can be achieved in the presence of a catalytic amount of a rhodium complex. The reaction involves the decarbonylation of the aldehyde by the rhodium catalyst, and the successive carbonylation of an organic halide utilizing the rhodium carbonyl that is formed in situ. Aldehydes having electron-withdrawing groups showed a higher ability to donate the carbonyl moiety. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.08.038

文献信息

• Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio
  作者：El-ichi Negishi、Christophe Copéret、Takumichi Sugihara、Izumi Shimoyama、Yantao Zhang、Guangzhong Wu、James M. Tour

  DOI：10.1016/s0040-4020(01)80765-1

  日期：1994.1

  The Pd-catalyzed carbonylative cyclization reaction involving omega-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-O ratio in the trapping with enolates.
• Catalytic generation and trapping of acylmetals containing Ni and Cu with enolates
  作者：Ei-ichi Negishi、Hidefumi Makabe、Izumi Shimoyama、Guangzhong Wu、Yantao Zhang

  DOI：10.1016/s0040-4020(97)10210-1

  日期：1998.2

  Carbonylative cyclization of iodoarenes and iodoalkenes containing a proximal enolate precursor can selectively provide either cyclic ketones or lactones in the presence of Ni or Cu catalysts via trapping of putative acylmetal derivatives with C-or O-enolates, respectively; the ring size and regioselectivity of the reaction may be predicted based on two generalizations derived from the recently developed corresponding Pd-catalyzed reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Carbonylative cyclization via intramolecular trapping of acylmetal derivatives by carbon nucleophiles catalyzed by late transition metals
  作者：Eiichi Negishi、Yantao Zhang、Izumi Shimoyama、Guangzhong Wu

  DOI：10.1021/ja00202a055

  日期：1989.9
• NEGISHI, EI-ICHI;ZHANG, YANTAO;SHIMOYAMA, IZUMI;WU, GUANGZHONG, J. AMER. CHEM. SOC., 111,(1989) N0, C. 8018-8020
  作者：NEGISHI, EI-ICHI、ZHANG, YANTAO、SHIMOYAMA, IZUMI、WU, GUANGZHONG

  DOI：——

  日期：——