3-methylene-5-phenylpyrrolidin-2-one | 125216-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-methylene-5-phenylpyrrolidin-2-one
• 英文别名: α-methylene-γ-phenyl-γ-butyrolactam；3-Methylene-5-phenyl-2-pyrrolidinone；3-methylidene-5-phenylpyrrolidin-2-one
• CAS: 125216-87-7
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: DYBMPCLGVBHOOK-UHFFFAOYSA-N

物化性质

• 沸点：
  364.2±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methylene-5-phenylpyrrolidin-2-one 生成 (-)-(R)-3-methylene-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  LIENNE, M.;MACAUDIERE, P.;CAUDE, M.;ROSSET, R.;TAMRUTE, A., CHIRALITY, 1,(1989) N, C. 45-56

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Benzylidenamino-2-phenylaethanol 在 盐酸 、 氯化亚砜 、 硫酸 、 四丁基硫酸氢铵 、 silica gel 、 甲基磺酰氯 、 三乙胺 作用下， 以 硝基甲烷 为溶剂， 生成 3-methylene-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Stereocontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethy])acrylates to imines using β-aminoalcohols as chiral auxiliaries.

  摘要：

  Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).

  DOI：

  10.1016/s0957-4166(00)80253-0

文献信息

• Conjugate reduction of α,β-unsaturated esters and amides with tributyltin hydride in the presence of magnesium bromide diethyl etherate
  作者：Satomi Hirasawa、Yoshie Tajima、Yoko Kameda、Hajime Nagano

  DOI：10.1016/j.tet.2007.08.059

  日期：2007.11

  We report herein that the conjugate reduction of α,β-unsaturated esters and amides, such as aryl acrylates, pantolactone esters of acrylic acids, diethyl itaconate and N-crotonylcamphorsultam, with tributyltin hydride proceeded in moderate to high yields in the presence of magnesium bromide diethyl etherate. The effect of metal halide enhancing the yields is also described.

  我们在此报告，在溴化镁存在下，α-β-不饱和酯和酰胺（如丙烯酸芳基酯，丙烯酸的泛内酯，丙烯酸衣康酸酯和N-巴豆基樟脑樟脑）与氢化三丁基锡的共轭还原反应以中等至高收率进行二乙醚。还描述了金属卤化物提高产率的作用。
• Highly cis- and trans-selective alkyl radical addition to α-methylene-γ-phenyl-γ-butyrolactams
  作者：Tomoko Yajima、Masako Hamano、Hajime Nagano

  DOI：10.1016/j.tetlet.2009.01.007

  日期：2009.3

  The 1,3-asymmetric induction in alkyl radical additions to α-methylene-γ-phenyl-γ-butyrolactams was investigated. The reactions of N-unsubstituted lactam using (Me3Si)3SiH under UV irradiation give cis-α,γ-disubstituted lactams, whereas reactions of N-pivaloyllactams using Et3B and Bu3SnH in the presence of Yb(OTf)3 give trans-α,γ-disubstituted lactams, both with high diastereoselectivities.

  研究了α-亚甲基-γ-苯基-γ-丁内酰胺的烷基加成中的1,3-不对称诱导。在紫外线照射下，使用（Me 3 Si）3 SiH的N-未取代内酰胺的反应产生了顺式-α，γ-二取代的内酰胺，而在Yb（OTf）存在下，使用Et 3 B和Bu 3 SnH的N-戊内酰胺的反应3得到具有高非对映选择性的反式-α，γ-二取代的内酰胺。
• Fouquet, Eric; Pereyre, Michel; Rodriguez, Alain L., Bulletin de la Societe Chimique de France, 1997, vol. 134, # 10,11, p. 959 - 968
  作者：Fouquet, Eric、Pereyre, Michel、Rodriguez, Alain L.、Roulet, Thomas

  DOI：——

  日期：——
• Alami, Najat Ei; Belaud, Chantal; Villieras, Jean, Synthetic Communications, 1988, vol. 18, # 16-17, p. 2073 - 2082
  作者：Alami, Najat Ei、Belaud, Chantal、Villieras, Jean

  DOI：——

  日期：——
• Enantioselective Synthesis of α-Methylene-γ-butyrolactams Using N-tert-Butanesulfinamides
  作者：Miguel Yus、Francisco Foubelo、Haythem K. Dema

  DOI：10.3987/com-10-s(e)94

  日期：——

  Indium-mediated coupling of ethyl 2-(bromomethyl)acrylate (1) and chiral N-tert-butanelsulfinylimines 2 in a saturated sodium bromide aqueous solution leads to N-tert-butanesulfinyl aminoesters 3 in high yields and diastereoselectivities. After column chromatography purification, enantiomerically pure aminoesters 3 were converted into the expected alpha-methylene-gamma-butyrolactams 4 in a one-pot process.