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(3R*,5S*)-2,5-dimethyl-3,5-diphenylisoxazolidine | 110317-60-7

中文名称
——
中文别名
——
英文名称
(3R*,5S*)-2,5-dimethyl-3,5-diphenylisoxazolidine
英文别名
(+/-)-cis-2,5-dimethyl-3,5-diphenylisoxazolidine;(3R,5S)-2,5-dimethyl-3,5-diphenyl-1,2-oxazolidine
(3R*,5S*)-2,5-dimethyl-3,5-diphenylisoxazolidine化学式
CAS
110317-60-7
化学式
C17H19NO
mdl
——
分子量
253.344
InChiKey
PKNIPRFWOASSTK-SJORKVTESA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    358.3±52.0 °C(Predicted)
  • 密度:
    1.066±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.7
  • 重原子数:
    19
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.29
  • 拓扑面积:
    12.5
  • 氢给体数:
    0
  • 氢受体数:
    2

SDS

SDS:110265264fd51f93075150fe8b699336
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反应信息

  • 作为反应物:
    描述:
    (3R*,5S*)-2,5-dimethyl-3,5-diphenylisoxazolidine 在 sodium hydride 作用下, 以 四氢呋喃 为溶剂, 反应 7.5h, 生成 (3E)-2,4-diphenylbut-3-en-2-ol
    参考文献:
    名称:
    Ring-opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts
    摘要:
    5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.
    DOI:
    10.3987/com-92-6239
  • 作为产物:
    描述:
    N-methyl-α-phenylnitrone2-苯基-1-丙烯甲苯 为溶剂, 反应 51.0h, 以23%的产率得到(3R*,5S*)-2,5-dimethyl-3,5-diphenylisoxazolidine
    参考文献:
    名称:
    Kinetic Resolution of Isoxazolidines by a Pd−BINAP Complex
    摘要:
    Asymmetric decomposition of isoxazolidine derivatives under catalysis by optically active palladium(ii) complexes was examined. When racemic ethyl cis-2,5-dimethyl-5-phenylisoxazolidine-3-carboxylate (cis-1a) was treated with a catalytic amount of [Pd(MeCN)(2){(S)-TolBINAP}](BF4)2 in CH2Cl2 for 60 h, optically active substrate was recovered with 99% ee and in 48% yield. The highest selectivity was achieved on treatment of racemic ethyl trans-2,4-dimethyl-5,5-diphenylisoxazolidine-3-carboxylate, to give the optically active substrate in 74% yield with 35% ee. The k(f)/k(s) value of this reaction reaches as high as 732. For this decomposition, each substrate should have both a methyl group on the 2-position and an alkoxycarbonyl group on the 3-position of the isoxazolidine ring. The enantioselectivities of the recovered substrates were influenced not only by the other substituent groups on the 4- and 5-positions but also by the geometrical structures of the substrates.
    DOI:
    10.1002/1099-0690(200211)2002:22<3855::aid-ejoc3855>3.0.co;2-4
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文献信息

  • Liguori, Angelo; Romeo, Giovanni; Sindona, Giovanni, Chemische Berichte, 1988, vol. 121, p. 105 - 110
    作者:Liguori, Angelo、Romeo, Giovanni、Sindona, Giovanni、Uccella, Nicola
    DOI:——
    日期:——
  • Ring-opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts
    作者:Ugo Chiacchio、Angelo Liguori、Giovanni Romeo、Giovanni Sindona、Nicola Uccella
    DOI:10.3987/com-92-6239
    日期:——
    5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.
  • Kinetic Resolution of Isoxazolidines by a Pd−BINAP Complex
    作者:Tetsuo Ohta、Hiroyuki Kamizono、Aya Kawamoto、Kazushige Hori、Isao Furukawa
    DOI:10.1002/1099-0690(200211)2002:22<3855::aid-ejoc3855>3.0.co;2-4
    日期:2002.11
    Asymmetric decomposition of isoxazolidine derivatives under catalysis by optically active palladium(ii) complexes was examined. When racemic ethyl cis-2,5-dimethyl-5-phenylisoxazolidine-3-carboxylate (cis-1a) was treated with a catalytic amount of [Pd(MeCN)(2)(S)-TolBINAP}](BF4)2 in CH2Cl2 for 60 h, optically active substrate was recovered with 99% ee and in 48% yield. The highest selectivity was achieved on treatment of racemic ethyl trans-2,4-dimethyl-5,5-diphenylisoxazolidine-3-carboxylate, to give the optically active substrate in 74% yield with 35% ee. The k(f)/k(s) value of this reaction reaches as high as 732. For this decomposition, each substrate should have both a methyl group on the 2-position and an alkoxycarbonyl group on the 3-position of the isoxazolidine ring. The enantioselectivities of the recovered substrates were influenced not only by the other substituent groups on the 4- and 5-positions but also by the geometrical structures of the substrates.
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