dimethyl 2-(iodomethyl)cyclopentane-1,1-dicarboxylate | 120790-36-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 2-(iodomethyl)cyclopentane-1,1-dicarboxylate
• CAS: 120790-36-5
• 化学式: C₁₀H₁₅IO₄
• 分子量: 326.131
• InChiKey: JFVYIDHXNJYTDD-UHFFFAOYSA-N

物化性质

• 沸点：
  304.8±12.0 °C(Predicted)
• 密度：
  1.612±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  dimethyl 2-(iodomethyl)cyclopentane-1,1-dicarboxylate 以 甲苯 为溶剂， 反应 8.0h， 以84%的产率得到(3aα,6aα)-dihydro-6a-carbomethoxycyclopentafuran-1(3H)-one
  参考文献：
  名称：

  Atom transfer cyclization reactions of .alpha.-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closures

  摘要：

  DOI：

  10.1021/jo00274a034
• 作为产物：
  描述：

  2-[2,2-Bis(methoxycarbonyl)cyclopentyl]acetic acid 在 lead(IV) acetate 、 sodium iodide 、 lithium chloride 作用下， 生成 dimethyl 2-(iodomethyl)cyclopentane-1,1-dicarboxylate
  参考文献：
  名称：

  碳离子引起的2-氧杂环丁烷分子内β裂解反应

  摘要：

  已经证明了β-内酯或2-氧杂环丁烷通过稳定的烯醇化物的分子内β-切割反应。已经制备了三元，四元，五元和六元碳环。

  DOI：

  10.1016/0040-4039(94)88396-3

文献信息

• Ionic iodocarbocyclization reaction
  作者：Osamu Kitagawa、Tadashi Inoue、Takeo Taguchi

  DOI：10.1016/0040-4039(92)88168-5

  日期：1992.4

  Iodocarbocyclization reactions of dimethyl alkenylmalonates in the presence of I2 and Ti(Ot-Bu)4 proceed in a regioselective and stereospecific manner through an ionic mechanism.

  在I 2和Ti（Ot-Bu）4存在下，烯丙基丙二酸二甲酯的碳碳环化反应通过离子机理以区域选择性和立体有择方式进行。
• Ionic iodocarbocyclization reactions of 4-alkenyl- and 4-alkynylmalonate derivatives
  作者：Osamu Kitagawa、Tadashi Inoue、Keiko Hirano、Takeo Taguchi

  DOI：10.1021/jo00063a033

  日期：1993.5

  The cyclization reactions of dimethyl 4-alkenylmalonate derivatives la-d in the presence Of 12 and Ti(Ot-Bu)4 proceed in a highly regio- and stereocontrolled manner (5-exo cyclization and trans addition) to give (iodoalkyl)cyclopentane derivatives 2 or bicyclic lactones 3 through the displacement of the iodide of 2 by an ester group. Iodocarbocyclization reactions of dimethyl [(cycloalkenyl)alkyl]malonates 1g-i or dimethyl [(methylenecycloalkyl)alkyl]malonates 1j and 1k proceed regio- and stereoselectively to give fused ring compounds or spiro compounds, respectively, as single isomers. Similar reactions of 4-alkynyl derivatives 5 give preferentially E-iodomethylene cyclopentane derivatives 6. An ionic mechanism rather than a radical mechanism is suggested on the basis of the regioselectivity and stereospecificity of the above reactions.
• Carbocyclization Reaction of Active Methine Compounds with Unactivated Alkenyl or Alkynyl Groups Mediated by TiCl₄−Et₃N
  作者：Osamu Kitagawa、Takashi Suzuki、Tadashi Inoue、Yoko Watanabe、Takeo Taguchi

  DOI：10.1021/jo981603k

  日期：1998.12.1

  In the presence of TiCl4, Et3N, and I-2, iodocarbocyclization reaction of various active methine compounds having alkenyl groups gave iodocycloalkane derivatives in good yields. On the other hand, TiCl4 and Et3N promote the carbocyclization of active methine compounds with 4-alkynyl groups in the absence of I-2 to give methylenecyclopentane derivatives in good yields. This reaction proceeds with high streoselectivity through a cis-addition of trichlorotitanium enolates of active methine compounds to alkynes, and the resulting vinyltitanium intermediates can be further functionalized by the reaction with various electrophiles.
• CURRAN, D. P.;CHANG, CHI-TAI, TETRAHEDRON LETT., 31,(1990) N, C. 933-936
  作者：CURRAN, D. P.、CHANG, CHI-TAI

  DOI：——

  日期：——