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(1S,2R)-2-nitro-1-phenylpropyl ethanethioate | 1397266-25-9

中文名称
——
中文别名
——
英文名称
(1S,2R)-2-nitro-1-phenylpropyl ethanethioate
英文别名
S-[(1S,2R)-2-nitro-1-phenylpropyl] ethanethioate
(1S,2R)-2-nitro-1-phenylpropyl ethanethioate化学式
CAS
1397266-25-9
化学式
C11H13NO3S
mdl
——
分子量
239.295
InChiKey
BTAUDCYZWXUCOZ-LDYMZIIASA-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

计算性质

  • 辛醇/水分配系数(LogP):
    2.4
  • 重原子数:
    16
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    88.2
  • 氢给体数:
    0
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    (1S,2R)-2-nitro-1-phenylpropyl ethanethioate甲酸 、 Pd(OH)2/C 、 氢气双氧水 作用下, 以 四氢呋喃甲醇 为溶剂, 反应 48.0h, 生成 (1S,2R)-2-amino-1-phenylpropanesulfonic acid
    参考文献:
    名称:
    Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes
    摘要:
    在手性方酰胺有机催化剂的催化下,描述了硫代乙酸与δ,δ²-二取代硝基烯的高对映和非对映选择性磺-迈克尔加成反应。这种有机催化反应的催化剂负载量极低(0.2 摩尔%),却能以极好的产率、良好的非对映选择性和较高的对映选择性(高达 94â:â6 dr,95% ee)合成出有用的δ-硝基硫化物。此外,该催化反应可以在 10 克的规模上进行,而且还能方便地转化为牛磺酸衍生物。
    DOI:
    10.1039/c2ob26068a
  • 作为产物:
    描述:
    硫代乙酸1-苯基-2-硝基丙烯三正丁胺 作用下, 以 氯仿 为溶剂, 反应 1.0h, 以25%的产率得到S-2-nitro-1-phenylpropyl thiolacetate
    参考文献:
    名称:
    Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins
    摘要:
    Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule. (C) 2012 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.tet.2012.01.031
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文献信息

  • Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins
    作者:Ning Chen、Jiaxi Xu
    DOI:10.1016/j.tet.2012.01.031
    日期:2012.3
    Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule. (C) 2012 Elsevier Ltd. All rights reserved.
  • Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes
    作者:Wen Yang、Da-Ming Du
    DOI:10.1039/c2ob26068a
    日期:——
    A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). In addition, the catalytic reaction can be performed on a 10 gram scale, and facile transformation into taurine derivative is also presented.
    在手性方酰胺有机催化剂的催化下,描述了硫代乙酸与δ±,δ²-二取代硝基烯的高对映和非对映选择性磺-迈克尔加成反应。这种有机催化反应的催化剂负载量极低(0.2 摩尔%),却能以极好的产率、良好的非对映选择性和较高的对映选择性(高达 94â:â6 dr,95% ee)合成出有用的δ-硝基硫化物。此外,该催化反应可以在 10 克的规模上进行,而且还能方便地转化为牛磺酸衍生物。
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