10,11-Dihydro-10,11-dihydroxy-5H-dibenzocyclohepten | 40462-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 10,11-Dihydro-10,11-dihydroxy-5H-dibenzocyclohepten
• 英文别名: Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-9,10-diol
• CAS: 40462-47-3
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: NCRHUZUIKXAFHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10,11-Dihydro-10,11-dihydroxy-5H-dibenzocyclohepten 、 三甲基乙酸酐 在 molybdenium(VI) dioxodichloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以91%的产率得到trans-11-(2,2-dimethylpropanoyloxy)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species

  摘要：

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.

  DOI：

  10.1021/jo048363v
• 作为产物：
  描述：

  10,11-dihydro-10,11-epoxy-5H-dibenzocycloheptene 、 乙醇 、 氢氧化钾 生成 10,11-Dihydro-10,11-dihydroxy-5H-dibenzocyclohepten
  参考文献：
  名称：

  BELLUCCI, G.;BERTI, G.;CHIAPPE, C.;FABRI, F.;MARIONI, F., J. ORG. CHEM., 54,(1989) N, C. 968-970

  摘要：

  DOI：

文献信息

• BELLUCCI, G.;BERTI, G.;CHIAPPE, C.;FABRI, F.;MARIONI, F., J. ORG. CHEM., 54,(1989) N, C. 968-970
  作者：BELLUCCI, G.、BERTI, G.、CHIAPPE, C.、FABRI, F.、MARIONI, F.

  DOI：——

  日期：——
• US6541659B1
  申请人：——

  公开号：US6541659B1

  公开（公告）日：2003-04-01
• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.