(E)-2-Methyl-3-phenyl-2-propen-1-ol-tetrahydro-2-pyranylether | 77301-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-2-Methyl-3-phenyl-2-propen-1-ol-tetrahydro-2-pyranylether
• 英文别名: 2-[(E)-2-methyl-3-phenylprop-2-enoxy]oxane
• CAS: 77301-62-3
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: ZYRYKVIMRAIOIA-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Methyl-3-phenyl-2-propen-1-ol-tetrahydro-2-pyranylether 在 三乙基硼 、 苄基三乙基氯化铵 甲醇 、 potassium fluoride 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 jones' reagent 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 ((1S,2R,3R)-2-chloro-1-methyl-3-phenylcyclopropyl)methanol
  参考文献：
  名称：

  Synthesis and stereostructure–activity relationship of a synthetic pyrethroid, 2-chloro-1-methyl-3-phenylcyclopropylmethyl-3-phenoxybenzyl ether

  摘要：

  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.

  DOI：

  10.1039/p19960001243
• 作为产物：
  描述：

  ethyl 2-methylcinnamate 在 盐酸 、 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 10.5h， 生成 (E)-2-Methyl-3-phenyl-2-propen-1-ol-tetrahydro-2-pyranylether
  参考文献：
  名称：

  Huelskaemper, Ludwig; Weyerstahl, Peter, Chemische Berichte, 1981, vol. 114, # 2, p. 746 - 756

  摘要：

  DOI：

文献信息

• Synthesis of 2,5-Diaryl-3-halofurans via Regioselective Ring Cleavage of Aryl 3-Aryl-2,2-dihalocyclopropyl Ketones
  作者：Yoo Tanabe、Ken-ichi Wakimura、Yoshinori Nishii、Yukari Muroya

  DOI：10.1055/s-1996-4218

  日期：1996.3

  Several aryl 3-aryl-2,2-dihalocyclopropyl ketones were converted to 2,5-diaryl-3-halofurans in the presence of aluminum chloride via regioselective gem-dihalocyclopropane ring cleavage. Friedel-Crafts acylation of substituted benzenes with 3-aryl-2,2-dihalocyclopropanecarbonyl chlorides followed by this furan formation also proceeded in a one-pot manner. For functionalization, bromine on a furan ring was easily replaced by methyl and carboxyl groups; lithiation using butyllithium followed by the treatment with iodomethane and carbon dioxide, respectively.

  在有氯化铝存在的情况下，通过区域选择性的宝石-二环丙烷环裂解，一些芳基 3-芳基-2,2-二环丙基酮被转化为 2,5-二芳基-3-卤呋喃。用 3-芳基-2,2-二卤代环丙烷羰酰氯对取代苯进行弗里德尔-卡夫酰化，然后形成呋喃，也是以一锅法进行的。在官能化方面，呋喃环上的溴很容易被甲基和羧基取代；使用丁基锂进行锂化，然后分别用碘甲烷和二氧化碳进行处理。
• Highly Stereoselective Radical Carbonylations of <i>gem</i>-Dihalocyclopropane Derivatives with CO
  作者：Yoshinori Nishii、Takao Nagano、Hideki Gotoh、Ryohei Nagase、Jiro Motoyoshiya、Hiromu Aoyama、Yoo Tanabe

  DOI：10.1021/ol062673d

  日期：2007.2.1

  A couple of radical carbonylations of gem-dihalocyclopropanes 1 using CO and Bu3SnH (formylation) or Bu3Sn(CH2CHCH2) (allylacylation) successfully proceeded to give trans and cis adducts (2 and 3) with good to excellent stereoselectivity (trans/cis = > 99/1-75/25 or 17/83-1/99). The formylation of 2,3-cis-disubstituted 1,1-dihalocyclopropanes enhanced trans selectivity (trans/cis = > 99/1-95/5), whereas both 2,3-cis-disubstituted and 2-monosubstituted 1,1-dihalocyclopropanes underwent allylacylation with nearly complete trans selectivity (trans/cis = > 99/1). Inherently less reactive gem-dichloro- and bromochlorocyclopropanes than gem-dibromocyclopropanes served as favorable substrates.
• Nishii, Yoshinori; Matsumura, Hiroshi; Muroya, Yukari, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 7, p. 1355 - 1357
  作者：Nishii, Yoshinori、Matsumura, Hiroshi、Muroya, Yukari、Tsuchiya, Toru、Tanabe, Yoo

  DOI：——

  日期：——
• HUELSKAEMPER L.; WEYERSTAHL P., CHEM. BER., 1981, 114, NO 2, 746-756
  作者：HUELSKAEMPER L.、 WEYERSTAHL P.

  DOI：——

  日期：——