5,7-dihydro-dibenzo[a,c]cycloheptene-6,6-dicarboxylic acid diethyl ester | 6672-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,7-dihydro-dibenzo[a,c]cycloheptene-6,6-dicarboxylic acid diethyl ester
• 英文别名: diethyl dibenzo[a,c]-1,3-cycloheptadiene-6,6-dicarboxylate；5,7-dihydro-dibenzo[a,c]cycloheptene-6,6-dicarboxylic acid diethyl ester；5,7-Dihydro-dibenzo[a,c]cyclohepten-6,6-dicarbonsaeure-diaethylester；Diethyl tricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaene-9,9-dicarboxylate
• CAS: 6672-66-8
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: MCICCDVKPJFFQG-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  451.6±35.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dihydro-dibenzo[a,c]cycloheptene-6,6-dicarboxylic acid diethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 5,7-Dihydro-dibenzo[a,c]cycloheptene-6,6-dicarboxylic acid ethyl ester
  参考文献：
  名称：

  Bis-Substituted Malonic Acid Hydroxamate Derivatives as Inhibitors of Human Neutrophil Collagenase (MMP8)

  摘要：

  Malonic acid hydroxamate derivatives bis-substituted at the methylene group were synthesized as potential nonpeptidic inhibitors of human neutrophil collagenase (MMP8). The presence of an aromatic residue both at the C2 malonic acid position and in the C-terminal tail for hydrophobic interactions with the surface-exposed S1 binding site and the S1' pocket of the enzyme, respectively, was found to be sufficient for submicromolar inhibition potencies. For optimal insertion of the aryl amide group into the hydrophobic S1' pocket, spacing of the C-terminal phenyl group by at least a SC-chain was required. In view of these results the achiral indan-2,2-dicarboxylic acid was used to mimic the 2-benzyl-2-methylmalonic acid residue, and its derivatization to the 3-phenylpropyl amide hydroxamate produced a potent, achiral, low-mass inhibitor of MMP8 (K-i = 0.3 mu M), the binding mode of which was unambiguously determined by X-ray crystallographic analysis.

  DOI：

  10.1021/jm980112p
• 作为产物：
  描述：

  2,2-Bis-(2-trimethylstannanyl-benzyl)-malonic acid diethyl ester 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以78%的产率得到5,7-dihydro-dibenzo[a,c]cycloheptene-6,6-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  CuCl-Mediated Intramolecular Oxidative Coupling of Aryl- and Alkenyltrimethylstannane Functions

  摘要：

  [GRAPHICS]The syntheses of bis-trimethylstannanes 8, 10, 12-14, 16, 18, 21, and 22 are described, Treatment of these substances with similar to 5 equiv of CuCl in DMF at rt for 30-60 min effects, in each case, oxidative coupling between the two sp(2) carbon centers bearing the Me3Sn function to produce good-to-excellent yields of tricyclic products 23-31, respectively.

  DOI：

  10.1021/ol9903988

文献信息

• Synthesis of novel C2-symmetric chiral bis(oxazoline) ligands and their application in the enantioselective addition of diethylzinc to aldehydes
  作者：Bin Fu、Da-Ming Du、Jianbo Wang

  DOI：10.1016/j.tetasy.2003.11.006

  日期：2004.1

  Novel chiral bis(oxazoline) ligands bearing dibenzo[a,c]cycloheptadiene and a dihydroxy group have been synthesized and their application in the catalytic asymmetric addition of diethylzinc to aldehydes investigated. The enantioselectivities for the aromatic aldehydes are generally high and up to 96% ee was obtained.

  合成了带有二苯并[ a，c ]环庚二烯和二羟基的新型手性双（恶唑啉）配体，并研究了它们在催化二乙基锌不对称加成醛中的应用。芳族醛的对映选择性通常很高，并且获得了高达96％的ee。
• Novel chiral dibenzo[a,c]cycloheptadiene bis(oxazoline) and catalytic enantioselective cyclopropanation of styrene
  作者：Da-Ming Du、Bin Fu、Wen-Ting Hua

  DOI：10.1016/s0040-4020(03)00144-3

  日期：2003.3

  A series of chiral C2-symmetric bis(oxazoline) ligands containing dibenzo[a,c]cycloheptadiene units were synthesized. The copper complexes, prepared in situ from copper (I)-triflate and the new enantiopure oxazoline ligands, were assessed as chiral catalysts in the enantioselective cyclopropanation of styrene with diazoacetate. Enantioselectivities up to 82 and 62%, respectively, for trans- and ci

  合成了一系列含有二苯并[ a，c ]环庚二烯单元的手性C 2对称双（恶唑啉）配体。由三氟甲磺酸铜（I）和新的对映体纯的恶唑啉配体原位制备的铜配合物在苯乙烯与重氮乙酸酯的对映选择性环丙烷化中被评估为手性催化剂。观察到反式和苯基-2-苯基环丙烷羧酸酯的对映选择性分别高达82％和62％。
• Palladium-Catalyzed (Ullmann-Type) Homocoupling of Aryl Halides:  A Convenient and General Synthesis of Symmetrical Biaryls via Inter- and Intramolecular Coupling Reactions
  作者：D. David Hennings、Tetsuo Iwama、Viresh H. Rawal

  DOI：10.1021/ol990872+

  日期：1999.10.1

  [GRAPHICS]A convenient new procedure is described for both inter- and intramolecular homocoupling of aryl halides (Ullmann reaction) using catalytic palladium in the presence of hydroquinone, a homogeneous reductant. Optimal conditions for the reductive coupling include the use of a 1:1 molar ratio of Pd(OAc)(2) and As(o-tolyl)(3) in catalytic amounts under basic conditions.
• Palladium‐catalyzed Intramolecular Coupling Reactions between Vinyl Bromides, Aryl and Vinyl Halides, and Aryl Iodides Mediated by Indium: Preparation of Five‐ to Eight‐membered Carbocycles and Heterocycles
  作者：Woo Hyung Jeon、Hyunseok Kim、Jang‐Sik Choi、Kooyeon Lee、Phil Ho Lee

  DOI：10.1002/bkcs.10106

  日期：2015.2
• Kenner, Journal of the Chemical Society, 1913, vol. 103, p. 625
  作者：Kenner

  DOI：——

  日期：——