trans-phenylcyclopropanocarbaldehyde | 34271-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-phenylcyclopropanocarbaldehyde
• 英文别名: (2-methyl-2-(2-methylprop-1-en-1-yl)cyclopropyl)benzene；1-methyl-2-phenylcyclopropane-1-carbaldehyde；trans-1-Methyl-2-phenylcyclopropan-aldehyd；(1R,2S)-1-methyl-2-phenylcyclopropane-1-carbaldehyde
• CAS: 34271-32-4
• 化学式: C₁₁H₁₂O
• mdl: MFCD18828532
• 分子量: 160.216
• InChiKey: PHEQDTOMKNXMHJ-QWRGUYRKSA-N

物化性质

• 沸点：
  242.4±29.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  trans-phenylcyclopropanocarbaldehyde 在 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 、 Ru(bpy)₃(PF₆)₂ 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 39.5h， 生成 2-methyl-1-(naphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  利用分子氧通过可见光促进氧化三取代烯烃直接合成烯酮

  摘要：

  描述了从烯烃一步合成烯酮。在分子氧和光催化剂存在下，在可见光照射下进行反应。该反应与各种类型的三取代烯烃一起进行，以高产率和高区域选择性得到烯酮。特别是，含氧和含氮的官能团、杂芳环和环丙烷是可以容忍的。机理研究和先前的报告表明，反应体系中产生的活性氧是单线态氧。

  DOI：

  10.1055/s-0040-1707150
• 作为产物：
  描述：

  反式-alpha-甲基肉桂醛 在 palladium diacetate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 trans-phenylcyclopropanocarbaldehyde
  参考文献：
  名称：

  O-Silylated steroidal cis-aminoalcohols as chiral auxiliaries: highly diastereoselective Pd-catalyzed cyclopropanation of α,β-unsaturated aldimines

  摘要：

  alpha,beta-Unsaturated imines, obtained from cis-17-silyloxy-16-amino steroids and alpha,beta-unsaturated aldehydes, react with diazomethane in the presence of a catalytic amount of Pd(OAc)(2) with high chemo- and diastereoselectivities to form steroidal cyclopropanocarbaldimines, chromatography on silica gel gives the substituted cyclopropanocarbaldehydes with a high enantiomeric excess and allows recovery of the chiral steroidal auxiliaries. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00334-9

文献信息

• The use of 1,2-O-isopropylidene-α-d-xylofuranose as a chiral auxiliary in asymmetric cyclopropanation reactions
  作者：José M. Vega-Pérez、Ignacio Periñán、Fernando Iglesias-Guerra

  DOI：10.1016/j.tetasy.2009.02.062

  日期：2009.5

  1,2-O-isopropylidene-d-xylofuranose, as a chiral auxiliary, is described. The Simmons–Smith cyclopropanation reaction of the corresponding alkenylidene derivatives with CH2I2/ZnEt2, in different reaction conditions, took place with high stereoselectivity. The diastereomeric excess in each case depended on the solvent and the temperature used in the reaction. The absolute configuration of the new stereogenic

  描述了衍生自作为手性助剂的1,2 - O-异亚丙基-d-木呋喃糖的环丙基亚甲基缩醛的立体选择性合成。在不同的反应条件下，相应的链烯基衍生物与CH 2 I 2 / ZnEt 2的Simmons-Smith环丙烷化反应具有很高的立体选择性。在每种情况下，非对映异构体过量取决于反应中所用的溶剂和温度。通过手性助剂的环丙烷部分的酸水解确定了形成的新的立体异构中心的绝对构型，该手性助剂也被回收了。
• Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
  作者：Nils L. Ahlburg、Oliver Hergert、Peter G. Jones、Daniel B. Werz

  DOI：10.1002/anie.202214390

  日期：2023.1.2

  A new class of donor-acceptor cyclopropanes bearing only a single, vinylogous acceptor moiety is presented. The system is capable of cycloadditions through Brønsted or Lewis acid catalysis with numerous reagents: aldehydes, ketones, thioketones, nitriles, naphth-2-ols, cyclopropanes, nitrones and isobenzofurans. The mechanism was explored in detail by kinetic and mechanistic experiments.

  提出了一类新的供体-受体环丙烷，其仅带有单个插烯受体部分。该系统能够通过布朗斯台德或路易斯酸催化与多种试剂进行环加成：醛、酮、硫酮、腈、萘-2-醇、环丙烷、硝酮和异苯并呋喃。通过动力学和机械实验详细探讨了该机制。
• Ligand‐Controlled Regiodivergence in Nickel‐Catalyzed Vinylcyclopropane Rearrangement
  作者：Keiichi Irifune、Ken Yamazaki、Takayuki Nakamuro、Masahiro Murakami、Tomoya Miura

  DOI：10.1002/anie.202307826

  日期：2023.8.14

  A Ni0-catalyzed rearrangement of 1,2-disubstituted 1-vinylcyclopropanes was studied. Either of the two product isomers, 1,4- or 1,5-disubstituted cyclopentenes, was selectively obtained depending on the choice of ligands. Experimental and computational investigations of the reaction revealed a clear insight into the origin of such high product selectivity.

  研究了Ni 0催化的1,2-二取代1-乙烯基环丙烷的重排。根据配体的选择选择性地获得两种产物异构体，1,4-或1,5-二取代的环戊烯。该反应的实验和计算研究揭示了对如此高产物选择性的起源的清晰见解。
• Scribe,P.; Wiemann,J., Bulletin de la Societe Chimique de France, 1971, p. 2268 - 2275
  作者：Scribe,P.、Wiemann,J.

  DOI：——

  日期：——
• Synthesis and stereostructure–activity relationship of a synthetic pyrethroid, 2-chloro-1-methyl-3-phenylcyclopropylmethyl-3-phenoxybenzyl ether
  作者：Yoshinori Nishii、Ken-ichi Wakimura、Toru Tsuchiya、Shogo Nakamura、Yoo Tanabe

  DOI：10.1039/p19960001243

  日期：——

  Of the four diastereoisomers of 2-chloro-1-methyl-3-phenylcyclopropylmet 3-phenoxybenzyl ether 5, a new type of synthetic pyrethroid, which have been synthesized, only the (1R*,2S*,3S*)-isomer 5a showed significant insecticidal activity against the tobacco cutworm and the common mosquito. Two enantiomers (1R,2S,3S)-(-)-5a and (1S,2R,3R)-(+)-5a were prepared by the optical resolution process, and their absolute configurations were determined by chemical derivatization via predictable asymmetric cyclopropanation. Bioassay showed that the (1R,2S,3S)-(-)-5a was active, while (1S,2R,3R)-(+)-5a was not. The geometry around the asymmetric centre of the (1R,2S,3S)-enantiomer was correlated with that of representative pyrethroids which are both optically active and have insecticidal activity.