2,2-dichloro-3,3,4,4-tetramethylcyclobutanone | 66239-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dichloro-3,3,4,4-tetramethylcyclobutanone
• 英文别名: 2,2-Dichloro-3,3,4,4-tetramethylcyclobutan-1-one
• CAS: 66239-90-5
• 化学式: C₈H₁₂Cl₂O
• 分子量: 195.089
• InChiKey: OYRGBEQRFXNGQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  2,2-dichloro-3,3,4,4-tetramethylcyclobutanone 生成 2,2,3,3-四甲基丁二酸
  参考文献：
  名称：

  A simple procedure for stereospecific vicinal dicarboxylation of olefins

  摘要：

  DOI：

  10.1021/jo00211a036
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 二氯乙烯酮 以61%的产率得到2,2-dichloro-3,3,4,4-tetramethylcyclobutanone
  参考文献：
  名称：

  Synthese selective d'acides glutariques a partir d'olefines

  摘要：

  DOI：

  10.1016/s0040-4039(01)93424-0

文献信息

• Titanium(IV) Chloride-Mediated Ring Cleavage and Michael Addition of 3,3-Dialkylcyclobutanones and 3-[(Trimethylsilyl)methyl]-cyclobutanones
  作者：Ryosuke Okuno、Jun-ichi Matsuo、Hiroyuki Ishibashi

  DOI：10.1248/cpb.60.793

  日期：——

  β′-Chloro and β′,γ′-unsaturated trichlorotitanium enolates, which were formed in situ by titanium(IV) chloride-mediated ring cleavage of 3,3-dialkylcyclobutanones and 3-[(trimethylsilyl)methyl]cyclobutanones, reacted with enones to give Michael adducts with keeping a labile β′-chloro or β′,γ′-unsaturated group.

  β′-氯和β′,γ′-不饱和的三氯钛烯醇盐，由四氯化钛介导的3,3-二烷基环丁酮和3-[(三甲基硅基)甲基]环丁酮的环裂解反应原位生成，与烯酮反应得到保留活泼β′-氯或β′,γ′-不饱和基团的迈克尔加合物。
• Facile Activation of Zinc. Preparation of Cyclobutanones via Dichloroketene and Cyclopropanes Using the Simmons-Smith Reaction
  作者：Yngve Stenstr⊘m

  DOI：10.1080/00397919208021545

  日期：1992.11

  Abstract Zinc powder activated by heating in an inert atmosphere gave good yields when used for the title reactions. The very easy work up procedure for the cyclobutanones further increases the potential of the method.

  摘要 在惰性气氛中加热活化的锌粉在用于标题反应时具有良好的产率。环丁酮的非常简单的后处理程序进一步增加了该方法的潜力。
• Synthesis of [1.1.1]Propellanes by Cyclization of 3-Alkylidenecyclobutylidenes
  作者：Monika Kenndoff、Andrea Singer、Günter Szeimies

  DOI：10.1002/prac.19973390141

  日期：——

  Starting from tricyclo[3.1.0.0(2,6)]hexane 5 and 1-bromobicyclo[1.1.0 ]butane 6, a series of [1.1.1]propellanes 15 and 21 has been synthesized which carry alkyl, aryl, alkenyl, and alkynyl groups. Propellane formation proceeded via 1-bromo-1-chloro-3-alkylidenecyclobutanes of type 13 and 19, which on treatment with methyllithium gave rise to the generation of carbenes 14 and 20 as short-lived intermediates. For these carbenes, the most efficient path of stabilization is obviously the intramolecular cycloaddition. Ab initio MO calculations at the Becke3LYP/6-31G* and MP2/6-31G* level of theory indicated that 3-alkylidenecyclobutylidenes 4 and 37a-d are not local energy minima but collapse to the corresponding [1.1.1]propellanes. On this basis, propellane formation should follow a carbenoid reaction path.
• DEPRES, JEAN-PIERRE;GREENE, ANDREW E., TETRAHEDRON LETT., 30,(1989) N0, C. 7065-7068
  作者：DEPRES, JEAN-PIERRE、GREENE, ANDREW E.

  DOI：——

  日期：——
• DEPRES, J. P.;COELHO, F.;GREENE, A. E., J. ORG. CHEM., 1985, 50, N 11, 1972-1973
  作者：DEPRES, J. P.、COELHO, F.、GREENE, A. E.

  DOI：——

  日期：——