1,2-C70H2 | 144240-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,2-C70H2
• 英文别名: (5,6)-Fullerene-C70;Fullerene C70；7,22-dihydro(C70-D5h(6))[5,6]fullerene
• CAS: 144240-52-8
• 化学式: C₇₀H₂
• 分子量: 842.786
• InChiKey: XTTGERWWUXSBNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  70
• 可旋转键数：
  0
• 环数：
  37.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  溴乙酸甲酯 、 1,2-C70H2 在 四丁基氢氧化铵 作用下， 以 甲醇 、 苯甲腈 为溶剂， 反应 120.0h， 以29%的产率得到methyl ([70]fulleren-1(2H)-yl)acetate
  参考文献：
  名称：

  制备C1-单烷基化的1,2-二氢[C 70 ]衍生物的方法：“其他”区域异构体的形成

  摘要：

  用TBAOH使1，2-C 70 H 2脱质子，然后用溴乙酸甲酯烷基化，导致形成C1-单烷基化的1，2-二氢-C 70衍生物。通过NMR光谱法确定烷基（C1）的位置，并与C2-单烷基化类似物的文献光谱进行比较。据推测，由于在C1处1,2-C 70 H 2的选择性去质子化，C1-烷基化是主要过程。除非仔细控制碱的量，否则用苄基溴代替溴乙酸甲酯会导致快速的二烷基化，在这种情况下，C1-单苄基化是主要过程。这种在C1上进行烷基化的方法是对C 70进行C2-单烷基化的方法的补充 含锌和溴乙酸甲酯。

  DOI：

  10.1021/jo030242s
• 作为产物：
  描述：

  富勒烯 在 水 、 铜 、 锌 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以27%的产率得到7,19,23,27,33,37,44,53-C70H8
  参考文献：
  名称：

  Preparation of C₇₀H₂, C₇₀H₄, and C₇₀H₈:  Three Independent Reduction Manifolds in the Zn(Cu) Reduction of C₇₀

  摘要：

  This article reports the preparation of C70Hn species by Zn(Cu) reduction. The major products were one isomer of C70H2, one major isomer of C70H4, and one major isomer of C70H8. Several minor products were detected by UV-Vis and/or mass spectrometry. The structures of the major products were assigned as 1,2-C70H2, 1,2,56,57-C70H4, and 7,19,23,27,33,37,44,53-C70H8. Interestingly, although the major isomer of C70H4 is generated by reduction of the major isomer of C70H2, the major isomer of C70H8 is not generated by reduction of the major isomer of C70H2 or C70H4 The evidence suggests that there are at least three different reduction manifolds operating. One manifold includes 1,2-C70H2 and 1,2,56,57-C70H4, major products in which highly pyramidalized bonds near the poles of C-70 are reduced. A second manifold includes 5,6-C70H2, a minor product. The third manifold consists of a set of C70H2, C70H4, and C70H6 species that are highly reactive and do not accumulate in solution. This third manifold leads to 7,19,23,27,33,37,44,53-C70H8. This third manifold is unique in that these compounds place hydrogens on nonadjacent carbons, a previously unobserved arrangement.

  DOI：

  10.1021/jo981627r

文献信息

• Preparation of C₇₀H₂, C₇₀H₄, and C₇₀H₈:  Three Independent Reduction Manifolds in the Zn(Cu) Reduction of C₇₀
  作者：H. Peter Spielmann、Guan-Wu Wang、Mark S. Meier、Brad R. Weedon

  DOI：10.1021/jo981627r

  日期：1998.12.1

  This article reports the preparation of C70Hn species by Zn(Cu) reduction. The major products were one isomer of C70H2, one major isomer of C70H4, and one major isomer of C70H8. Several minor products were detected by UV-Vis and/or mass spectrometry. The structures of the major products were assigned as 1,2-C70H2, 1,2,56,57-C70H4, and 7,19,23,27,33,37,44,53-C70H8. Interestingly, although the major isomer of C70H4 is generated by reduction of the major isomer of C70H2, the major isomer of C70H8 is not generated by reduction of the major isomer of C70H2 or C70H4 The evidence suggests that there are at least three different reduction manifolds operating. One manifold includes 1,2-C70H2 and 1,2,56,57-C70H4, major products in which highly pyramidalized bonds near the poles of C-70 are reduced. A second manifold includes 5,6-C70H2, a minor product. The third manifold consists of a set of C70H2, C70H4, and C70H6 species that are highly reactive and do not accumulate in solution. This third manifold leads to 7,19,23,27,33,37,44,53-C70H8. This third manifold is unique in that these compounds place hydrogens on nonadjacent carbons, a previously unobserved arrangement.
• Methodology for the Preparation of C1-Monoalkylated 1,2-Dihydro[C₇₀] Derivatives:  Formation of the “Other” Regioisomer
  作者：Zhongwen Wang、Mark S. Meier

  DOI：10.1021/jo030242s

  日期：2004.3.1

  Deprotonation of 1,2-C70H2 with TBAOH, followed by alkylation with methyl bromoacetate, results in formation of a C1-monoalkylated 1,2-dihydro-C70 derivative. The position of the alkyl group (C1) was established by NMR spectroscopy and comparison with literature spectra of C2-monoalkylated analogs. Presumably, C1-alkylation is the major process due to selective deprotonation of 1,2-C70H2 at C1. Substitution

  用TBAOH使1，2-C 70 H 2脱质子，然后用溴乙酸甲酯烷基化，导致形成C1-单烷基化的1，2-二氢-C 70衍生物。通过NMR光谱法确定烷基（C1）的位置，并与C2-单烷基化类似物的文献光谱进行比较。据推测，由于在C1处1,2-C 70 H 2的选择性去质子化，C1-烷基化是主要过程。除非仔细控制碱的量，否则用苄基溴代替溴乙酸甲酯会导致快速的二烷基化，在这种情况下，C1-单苄基化是主要过程。这种在C1上进行烷基化的方法是对C 70进行C2-单烷基化的方法的补充 含锌和溴乙酸甲酯。