exo-2-chlorobicyclo[2.2.1]heptane-2-carboxylic acid | 101774-57-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: exo-2-chlorobicyclo[2.2.1]heptane-2-carboxylic acid
• 英文别名: (+/-)-2-chloro-norbornane-2endo-carboxylic acid；(+/-)-2-Chlor-norbornan-2endo-carbonsaeure；(1R,2R,4S)-2-chlorobicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 101774-57-6
• 化学式: C₈H₁₁ClO₂
• 分子量: 174.627
• InChiKey: JUHQQBWZIAUSDN-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-2-chlorobicyclo[2.2.1]heptane-2-carboxylic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 exo-2-chlorobicyclo[2.2.1]heptane-2-(N-methyl)carboxamide
  参考文献：
  名称：

  亚氨基氮丙啶的合成，构型和15 N NMR光谱。合成子等同于卯木反应的三个组成部分†

  摘要：

  单环iminoaziridines和外切-内切个从降冰片烷衍生螺iminoaziridines的非对映体在向上的批次制备10g至培育应用如在合成的构建块。N，N'-二取代的α-卤代idine啶可从N-取代的α-卤代羧酰胺分两步轻松获得，并通过强碱（例如碱金属氢化物或叔丁醇）将1,3-脱卤化氢制得可蒸馏的油或-熔融固体，由标题化合物的E - Z非对映异构体缓慢互变组成。概述了该反应的范围和限制。配置E和Z是基于均一的1 H- 1 H偶合和不对称溶剂诱导的位移而分配的，它要求在13 C NMR光谱中，在亚氨基氮上观察到的取代基的γ效应是屏蔽的，这与孔相反所有其他类型的C N化合物中已知的屏蔽γ效应。但是，NOE NMR研究明确表明先前的分配是正确的，因此观察到的γ效应实际上会造成屏蔽作用。的范围15个ÑNMR化学位移跨越多于60ppm的。两种类型氮上取代基的β效应和γ效应均不遵循均匀的递增规律。

  DOI：

  10.1021/jo062213y
• 作为产物：
  描述：

  环戊二烯 在 乙醚 、 乙酸乙酯 、 铂 作用下， 生成 exo-2-chlorobicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Genetic and Biogeographic Relationships of the Invasive Round (Neogobius melanostomus) and Tubenose (Proterorhinus marmoratus) Gobies in the Great Lakes Versus Eurasian Populations

  摘要：

  Population genetic structure and systematic relationships were investigated for two exotic fishes introduced to the Great Lakes in 1990, the round goby Neogobius melanostomus and the tubenose goby Proterorhinus marmoratus, using DNA sequences from the left domain of the mitochondrial DNA control region. Samples of round gobies were compared from different sites in the Great Lakes, an introduced population from the Gulf of Gdansk in Poland, and a native population from the northern Black Sea. The round goby was characterized by, relatively high genetic variability, and 17 haplotypes were identified from 64 individuals. Levels of genetic variation for the round goby were similar in the invasive and native sampling sites, suggesting relatively large founding populations and lack of bottlenecks. The northern Black Sea was eliminated as a probable founding source for both the Great Lakes and the exotic population in Poland. Substitutions in the left domain of the control region revealed significant differences among samples from the Great Lakes and Eurasia, and between Lakes Erie and St. Clair, suggesting non-random mating. No variation was detected in the tubenose goby population in the Great Lakes, which has been less successful in terms of spread and population growth. A molecular clock calibration suggested that the genera Neogobius and Proterorhinus diverged about 5.2 +/- 1.0 million years ago, apparently separating from a common ancestor shared with Gobius during the isolation of the Paratethys basin from the Mediterranean Tethys Sea.

  DOI：

  10.1016/s0380-1330(01)70642-9

文献信息

• Synthesis, Configuration, and ¹⁵N NMR Spectra of Iminoaziridines. Synthons Equivalent to Three Components of the Ugi Reaction
  作者：Helmut Quast、Sven Aldenkortt、Bernd Freudenreich、Peter Schäfer、Manfred Hagedorn、Jens Lehmann、Klaus Banert

  DOI：10.1021/jo062213y

  日期：2007.3.1

  of slowly interconverting E−Z diastereomers of the title compounds. The scope and limitations are outlined for this reaction. The configurations E and Z that were assigned on the basis of homoallylic 1H−1H coupling and asymmetric solvent-induced shifts required that, in 13C NMR spectra, the observed γ-effects of substitutents at the imino nitrogens were deshielding, contrary to the well-known shielding

  单环iminoaziridines和外切-内切个从降冰片烷衍生螺iminoaziridines的非对映体在向上的批次制备10g至培育应用如在合成的构建块。N，N'-二取代的α-卤代idine啶可从N-取代的α-卤代羧酰胺分两步轻松获得，并通过强碱（例如碱金属氢化物或叔丁醇）将1,3-脱卤化氢制得可蒸馏的油或-熔融固体，由标题化合物的E - Z非对映异构体缓慢互变组成。概述了该反应的范围和限制。配置E和Z是基于均一的1 H- 1 H偶合和不对称溶剂诱导的位移而分配的，它要求在13 C NMR光谱中，在亚氨基氮上观察到的取代基的γ效应是屏蔽的，这与孔相反所有其他类型的C N化合物中已知的屏蔽γ效应。但是，NOE NMR研究明确表明先前的分配是正确的，因此观察到的γ效应实际上会造成屏蔽作用。的范围15个ÑNMR化学位移跨越多于60ppm的。两种类型氮上取代基的β效应和γ效应均不遵循均匀的递增规律。
• Genetic and Biogeographic Relationships of the Invasive Round (Neogobius melanostomus) and Tubenose (Proterorhinus marmoratus) Gobies in the Great Lakes Versus Eurasian Populations
  作者：Alison K. Dillon、Carol A. Stepien

  DOI：10.1016/s0380-1330(01)70642-9

  日期：2001.1

  Population genetic structure and systematic relationships were investigated for two exotic fishes introduced to the Great Lakes in 1990, the round goby Neogobius melanostomus and the tubenose goby Proterorhinus marmoratus, using DNA sequences from the left domain of the mitochondrial DNA control region. Samples of round gobies were compared from different sites in the Great Lakes, an introduced population from the Gulf of Gdansk in Poland, and a native population from the northern Black Sea. The round goby was characterized by, relatively high genetic variability, and 17 haplotypes were identified from 64 individuals. Levels of genetic variation for the round goby were similar in the invasive and native sampling sites, suggesting relatively large founding populations and lack of bottlenecks. The northern Black Sea was eliminated as a probable founding source for both the Great Lakes and the exotic population in Poland. Substitutions in the left domain of the control region revealed significant differences among samples from the Great Lakes and Eurasia, and between Lakes Erie and St. Clair, suggesting non-random mating. No variation was detected in the tubenose goby population in the Great Lakes, which has been less successful in terms of spread and population growth. A molecular clock calibration suggested that the genera Neogobius and Proterorhinus diverged about 5.2 +/- 1.0 million years ago, apparently separating from a common ancestor shared with Gobius during the isolation of the Paratethys basin from the Mediterranean Tethys Sea.