(3-methyloxiran-2-yl)(phenyl)methanone | 17180-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-methyloxiran-2-yl)(phenyl)methanone
• 英文别名: Methanone, (3-methyloxiranyl)phenyl-；(3-methyloxiran-2-yl)-phenylmethanone
• CAS: 17180-62-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: PJQWDBYGSUMUBT-UHFFFAOYSA-N

物化性质

• 沸点：
  260.2±33.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-methyloxiran-2-yl)(phenyl)methanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 84.5h， 生成 (1S,3S)-1-phenylbutane-1,3-diol
  参考文献：
  名称：

  Takeshita, Mitsuhiro; Miura, Masatomo; Unuma, Yukiko, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 2901 - 2906

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-methyl-oxiranyl)-phenyl-methanol 生成 (3-methyloxiran-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Indium-Promoted Chemo- and Diastereoselective Allylation of α,β-Epoxy Ketones with Potassium Allyltrifluoroborate

  摘要：

  A practical method for the chemo- and diastereoselective allylation of alpha,beta-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford alpha,beta-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.

  DOI：

  10.1021/ol1023757

文献信息

• A highly enantioselective asymmetric Darzens reaction catalysed by proline based efficient organocatalysts for the synthesis of di- and tri-substituted epoxides
  作者：Veeramanoharan Ashokkumar、Ayyanar Siva、R. Ramaswamy Chidambaram

  DOI：10.1039/c7cc06194c

  日期：——

  A new class of easily available and readily tunable proline based chiral organocatalysts was found to efficiently catalyse an unprecedented highly enantioselective asymmetric Darzens reaction of α-chloro ketones and substituted α-chloro ketones with various aldehydes, which directly produces optically active di- and tri-substituted chiral epoxides with higher product yields (up to 97 %) and excellent

  已发现一类新的易于获得且易于调节的脯氨酸基手性有机催化剂，可有效催化前所未有的高度对映选择性的α-氯酮和取代的α-氯酮与各种醛的不对称不对称Darzens反应，可直接产生光学活性的二-和三-在温和的反应条件下，取代的手性环氧化物具有较高的产品收率（高达97％）和优异的ee（高达99％）。
• Simple Synthetic Method of Allyl- and Vinyl-Epoxides by Allylation of Carbonyl Groups with Allylic Tins Catalyzed by PbI₂-HMPA
  作者：Ikuya Shibata、Shoji Fukuoka、Akio Baba

  DOI：10.1246/cl.1998.533

  日期：1998.6

  the chemoseletive allylation at the carbonyl groups of α-bromo ketones with allylic tin, where PbI2-HMPA effected as a chemoselective catalyst. Moreover, vinyl epoxides were obtained in one pot procedure by the PbI2-HMPA catalyzed reaction of γ-chloroallyltri-n-butyltin with aldehydes. Because of the mildness of the catalyst, the formed epoxide functionalities were not decomposed.

  烯丙基环氧化物是通过 α-溴酮的羰基与烯丙基锡的化学选择性烯丙基化来制备的，其中 PbI2-HMPA 作为化学选择性催化剂。此外，通过 PbI2-HMPA 催化 γ-氯烯丙基三正丁基锡与醛的反应，在一锅法中获得乙烯基环氧化物。由于催化剂的温和性，形成的环氧化物官能团没有分解。
• Selective oxidation with t-butyl hydroperoxide and aluminium reagents
  作者：Kazuhiko Takai、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)77778-1

  日期：1980.1

  Stereoselective epoxidation of allylic alcohols is achieved with organoaluminium peroxides. Transformation of secondary alcohols to ketones with same reagents is also disclosed.

  用有机铝过氧化物可以实现烯丙基醇的立体选择性环氧化。还公开了用相同的试剂将仲醇转化为酮。
• Novel synthesis of syn-α,β-epoxy alcohols by diastereoselective carbonyl reduction of α,β-epoxy ketones
  作者：Takayo Kawakami、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)78454-1

  日期：1994.11

  A novel tin hydride reagent, Bu3SnH-Bu4NCN, reduced α,β-epoxy ketones to the corresponding syn-α,β-epoxy alcohols in high diastereoselectivities.

  一种新型的氢化锡试剂Bu 3 SnH-Bu 4 NCN，可在高非对映选择性下将α，β-环氧酮还原为相应的顺式-α，β-环氧醇。
• A Highly Efficient Ruthenium-Catalyzed Rearrangement of α,β-Epoxyketones to 1,2-Diketones
  作者：Chia-Lung Chang、Manyam Praveen Kumar、Rai-Shung Liu

  DOI：10.1021/jo0303867

  日期：2004.4.1

  TpRuPPh3(CH3CN)2PF6 catalyzed the efficient rearrangement of α,β-epoxyketones to 1,2-diketones. Unlike a previously reported iron catalyst, the reaction in this case is applicable not only to 1,2-disubstituted epoxides but also to mono- and trisubstituted epoxides and tolerates oxygen functionalities. The sterically crowded and highly basic tris(1-pyrazolyl)borate (Tp) ligand of the ruthenium catalyst

  TpRuPPh 3（CH 3 CN）2 PF 6催化α，β-环氧酮高效重排为1,2-二酮。与先前报道的铁催化剂不同，在这种情况下，该反应不仅适用于1,2-二取代的环氧化物，而且适用于单和三取代的环氧化物，并具有氧官能度。钌催化剂的空间密集且高度碱性的三（1-吡唑基）硼酸酯（Tp）配体可能是其对1,2-二酮而不是1,3-二酮的高选择性的原因。