2-methylenecyclopropane-1-carbaldehyde | 142423-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-methylenecyclopropane-1-carbaldehyde
• 英文别名: 2-methylenecyclopropanecarboxaldehyde；2-methylenecyclopropanecarbaldehyde；Cyclopropanecarboxaldehyde, methylene-；2-methylidenecyclopropane-1-carbaldehyde
• CAS: 142423-24-3
• 化学式: C₅H₆O
• 分子量: 82.102
• InChiKey: RVDQZNUZKSPPND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-methylenecyclopropane-1-carbaldehyde 在 barium dihydroxide 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 (2S)-2-氨基-2-[(1S)-2-亚甲基环丙基]乙酸
  参考文献：
  名称：

  Synthesis of (±)-(2-Methylenecyclopropyl)glycine and (±)-4-[(Amino(carboxymethyl)]spiro[2.2]pentane-1-carboxylic Acid

  摘要：

  本文介绍了一种制备外消旋环丙基甘氨酸的简便方法，包括先氧化环丙基甲醇，然后进行布歇勒-伯格反应，并依次水解得到的海因。

  DOI：

  10.1055/s-2006-926320
• 作为产物：
  描述：

  (2-亚甲基环丙基)甲醇 在 草酰氯 、 二甲基亚砜 作用下， 以75%的产率得到2-methylenecyclopropane-1-carbaldehyde
  参考文献：
  名称：

  Synthesis of (±)-(2-Methylenecyclopropyl)glycine and (±)-4-[(Amino(carboxymethyl)]spiro[2.2]pentane-1-carboxylic Acid

  摘要：

  本文介绍了一种制备外消旋环丙基甘氨酸的简便方法，包括先氧化环丙基甲醇，然后进行布歇勒-伯格反应，并依次水解得到的海因。

  DOI：

  10.1055/s-2006-926320

文献信息

• Synthesis and Radical Polymerization of Various 2-Cyclopropylacrylates
  作者：Armin de Meijere、Viktor Bagutski、Frank Zeuner、Urs Karl Fischer、Volker Rheinberger、Norbert Moszner

  DOI：10.1002/ejoc.200400132

  日期：2004.9

  spectrometry and elemental analysis. The radical homopolymerizations of 1a−n were carried out with 2,2′-azabisisobutyronitrile (AIBN) as initiator in chlorobenzene at 65 °C. The highest polymer yields were obtained in the polymerizations of 1f and 1h or 1k and 1l, i.e. from monomers with an annelated five- or six-membered ring. In the case of 1h and 1k, both the polymer yields (99 and 98%, respectively) and

  通过应用标准转化，例如从醛形成氰醇、醇解为 α-羟基羧酸酯、α-氧代羧酸的氧化和 Wittig 亚甲基化，从容易获得的前体合成了十四种具有各种取代基 R1-R5 的新型 2-环丙烷基丙烯酸酯 1a-n酯。总产率为 33% 至 54%。开发了一种将环丙二甲酸二甲酯水解成相应半酯的新方法。α-氧代羧酸盐 7g-n 是通过四乙酸二铑催化烯烃 8g-n 与重氮丙酮酸甲酯或乙酯的环丙烷化反应制备的，产率为 32-58%。单体 1a-n 通过 1H、13C NMR 光谱、质谱和元素分析进行​​表征。1a-n 的自由基均聚是用 2 进行的，2'-氮杂二异丁腈 (AIBN) 作为引发剂在 65 °C 的氯苯中。在 1f 和 1h 或 1k 和 1l 的聚合中获得最高的聚合物产率，即来自具有退火五元或六元环的单体。在 1h 和 1k 的情况下，聚合物产率（分别为 99% 和 98%）以及 57 和 93 °C
• Synthesis of Novel α-Aminophosphonates Containing Small Rings
  作者：Tamara Kuznetsova、Nikolai Yashin、Elena Villemson、Andrey Chemagin、Elena Averina、Maria Kabachnik

  DOI：10.1055/s-2008-1032019

  日期：2008.2

  The synthesis of cyclopropyl- and cyclobutyl-substituted α-aminophosphonates by three-component microwave-assisted reaction of cyclopropanecarbaldehydes, benzylamine, and diethyl phosphite in the presence of cadmium iodide as catalyst has been developed.

  已经开发出一种合成环丙基和环丁基取代的β-氨基膦酸盐的方法，该方法通过在碘化镉作为催化剂的情况下，对环丙烷甲醛、苄胺和亚磷酸二乙酯进行三组分微波辅助反应。
• New Convenient Access to Optically Active Methylidenecyclopropylcarbinols
  作者：Maurice Le Corre、Alain Hercouet、Bernard Bessieres

  DOI：10.1021/jo00097a066

  日期：1994.9
• An Efficient Route to 2-Substituted<i>N</i>-(1-Amino-3-methylpyrrol)amides by Ring-Opening Cyclization of Benzylidene- and Alkylidenecyclopropylcarbaldehydes with Hydrazides
  作者：Xiang-Ying Tang、Min Shi

  DOI：10.1021/jo900730t

  日期：2009.8.21

  A convenient and efficient synthetic method for the construction of 2,3-disubstituted pyrrolamides in moderate to good Yields is established. The in situ generated water significantly accelerates the reaction rate. A possible mechanism involving the cascade ring-opening and thermal-induced rearrangement to produce the five-membered ring is proposed.
• Fluorinated methylenecyclopropane analogues of nucleosides. Synthesis and antiviral activity of (Z)- and (E)-9-{[(2-fluoromethyl-2-hydroxymethyl)-cyclopropylidene]methyl}adenine and -guanine
  作者：Chengwei Li、Mark N. Prichard、Brent E. Korba、John C. Drach、Jiri Zemlicka

  DOI：10.1016/j.bmc.2007.11.082

  日期：2008.3

  Synthesis and antiviral activity of the title fluoromethylenecyclopropane analogues 15a, 15b, 16a, and 16b is described. Methylenecyclopropane carboxylate was first transformed to 2,2-bis-hydroxymethylmethylenecyclopropane. Selective monoacetylation followed by introduction of fluorine gave 2-acetoxymethyl-2-fluoromethylmethylenecyclopropane as the key inter-mediate. The synthesis of analogues 15a, 15b, 16a, and 16b then followed alkylation-elimination procedure as described previously for other methylenecyclopropane analogues. The adenine Z-isomer 15a was found to be a potent inhibitor of Epstein-Barr virus (EBV) in vitro with EC50/CC50 (mu M) 0.5/55.7. Compounds 15b, 16a, and 16b were also active but at higher concentrations, EC50/CC50 (mu M) 3.2-7.5/53.6-64.1. Analogue 15a inhibited hepatitis C virus by virtue of its cytotoxicity and it moderately inhibited replication of the Towne strain of human cytomegalovirus (HCMV). The E-isomer 16a was a substrate for adenosine deaminase, whereas the Z-isomer 15a was not deaminated. (C) 2007 Elsevier Ltd. All rights reserved.