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肉桂基(乙基)硫烷 | 59277-53-1

中文名称
肉桂基(乙基)硫烷
中文别名
——
英文名称
Cinnamyl Ethyl Sulfide
英文别名
[(E)-3-ethylsulfanylprop-1-enyl]benzene
肉桂基(乙基)硫烷化学式
CAS
59277-53-1
化学式
C11H14S
mdl
——
分子量
178.298
InChiKey
HMTMMROZCGHPOZ-RMKNXTFCSA-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):
    3.7
  • 重原子数:
    12
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.27
  • 拓扑面积:
    25.3
  • 氢给体数:
    0
  • 氢受体数:
    1

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    SOME KNOEVENAGEL REACTIONS WITH ETHYLSULFONYLACETIC ACID
    摘要:
    DOI:
    10.1021/jo01365a006
  • 作为产物:
    描述:
    O-[(E)-3-phenylprop-2-enyl] ethylsulfanylmethanethioate 在 β-环糊精 作用下, 反应 126.0h, 以88%的产率得到肉桂基(乙基)硫烷
    参考文献:
    名称:
    Molecular Orbital Studies on Pericyclic Reactions of Cinnamyl Xanthates in .BETA.-Cyclodextrin Cavities.
    摘要:
    O-肉桂基 S-甲基二硫代碳酸酯(黄原酸酯,1a)的固体 β-环糊精(β-CyD)络合物在 45°C 下加热后发生不对称[3,3]-对称重排,得到光学 S-(1-苯基烯丙基)S-甲基二硫代碳酸酯(2a),ee 值为 60%。在 120°C 的温度下加热 2a 的 β-CyD 复合物会导致 COS 挤出,从而得到高产率的肉桂基甲基硫醚(3a)。根据分子轨道计算数据对反应行为和 β-CyD 的作用进行了讨论。
    DOI:
    10.1248/cpb.48.1652
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文献信息

  • SRS-A antagonists
    申请人:Lilly Industries Limited
    公开号:US04513005A1
    公开(公告)日:1985-04-23
    There are described pharmacologically active compounds, useful in the treatment of allergic/inflammatory disorders involving SRS-A as causal mediator and which, in free acid form, are of formula I, ##STR1## in which R.sub.1 is (i) an aliphatic, saturated or unsaturated hydrocarbyl radical of up to 20 carbon atoms, unsubstituted or substituted by at least one substituent selected from halogen, hydroxy, C.sub.3-6 alkoxy, C.sub.3-6 cycloalkyl, aryl or heteroaryl, the cycloalkyl, aryl or heteroaryl being unsubstituted or substituted by at least one substituent selected from hydroxy, halogen and alkyl, alkenyl or alkynyl of up to 10 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms unsubstituted or substituted by alkyl, alkenyl or alkynyl of up to 16 carbon atoms, or (iii) aryl or heteroaryl, unsubstituted or substituted by hydroxyl, C.sub.1-4 alkoxy, halogen or alkyl, alkenyl or alkynyl of up to 16 carbon atoms; and R.sub.2 is (i) alkyl, cycloalkyl or alkenyl of up to 10 carbon atoms, unsubstituted or substituted by one or more substituents selected from aryl, cycloalkyl, halogen, hydroxy, NHR.sub.3 and COX, where R.sub.3 is H, C.sub.1-4 alkyl, aryl or an amino acid residue or COX, and X is OH, C.sub.1-4 alkyl, NH.sub.2 or an amino acid residue, or (ii) aryl or heteroaryl, unsubstituted or substituted by one or more substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-5 acyl, halogen, hydroxy, carboxy, nitro, trihalomethyl, phenyl, C.sub.1-4 acylamino and NHR.sub.4, where R.sub.4 is hydrogen or C.sub.1-4 alkyl; and Y is --S--, --SO-- or --SO.sub.2 --, with the proviso that when --YR.sub.2 is glutathionyl, cysteinyl or cysteinylglycinyl, then R.sub.1 is other than an unsubstituted alkatetraenyl or alkapentaenyl radical of 12 to 16 carbon atoms.
    描述了在涉及SRS-A作为因果介质的过敏/炎症性疾病治疗中有用的药理活性化合物,这些化合物在游离酸形式下的化学式为I,其中R.sub.1是(i)具有多达20个碳原子的脂肪烃基、饱和或不饱和的烃基,未取代或被至少一种取代基取代,所述取代基选自卤素、羟基、C.sub.3-6烷氧基、C.sub.3-6环烷基、芳基或杂环芳基,所述环烷基、芳基或杂环芳基未取代或被至少一种取代基取代,所述取代基选自羟基、卤素和多达10个碳原子的烷基、烯基或炔基,(ii)具有3至8个碳原子的未取代或被多达16个碳原子的烷基、烯基或炔基取代的环烷基,或(iii)芳基或杂环芳基,未取代或被羟基、C.sub.1-4烷氧基、卤素或多达16个碳原子的烷基、烯基或炔基取代;R.sub.2是(i)多达10个碳原子的烷基、环烷基或烯基,未取代或被一个或多个取代基取代,所述取代基选自芳基、环烷基、卤素、羟基、NHR.sub.3和COX,其中R.sub.3为H、C.sub.1-4烷基、芳基或氨基酸残基或COX,X为OH、C.sub.1-4烷基、NH.sub.2或氨基酸残基,或(ii)芳基或杂环芳基,未取代或被一个或多个取代基取代,所述取代基选自C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.2-5酰基、卤素、羟基、羧基、硝基、三卤甲基、苯基、C.sub.1-4酰胺基和NHR.sub.4,其中R.sub.4为氢或C.sub.1-4烷基;Y为--S--、--SO--或--SO.sub.2--,但当--YR.sub.2为谱胱甘肽、半胱氨酸或半胱氨酰甘氨酸时,R.sub.1不是12至16个碳原子的未取代的α-四烯基或α-五烯基基团。
  • Stereoselective formation of allylic sulfides via two sequential (3,3)-sigmatropic rearrangements of allylic xanthates and its mechanistic aspects.
    作者:Kazunobu HARANO、Norihide OHIZUMI、Keisuke MISAKA、Shigeru YAMASHIRO、Takuzo HISANO
    DOI:10.1248/cpb.38.619
    日期:——
    O-(2-Alkynyl) S-alkyl dithiocarbonates (allylic xanthates) were pyrolyzed to give 2-alkenyl alkyl sulfides (allylic sulfides) via the corresponding allylically isomeric S-(2-alkenyl) S-alkyl dithiocarbonates. The reaction follows the first-order rate law with relatively low sensitivity to the ionizing power of the medium and sizeably negative entropies of activation. When a mixture of two dithiol esters having different S-(2-alkenyl) groups and different S-alkyl groups was pyrolyzed, a "cross product" was not observed. The reaction was found to be facilitated by the presence of phenolic compounds or Lewis acids.Based on these findings together with modified neglect of diatomic overlap (MNDO) calculation data, the mechanism for the formation reaction of 2-alkenyl alkyl sulfides is discussed.
    O-(2-炔基) S-烷基二硫代碳酸酯(烯丙基黄原酸酯)通过相应的烯丙异构S-(2-烯基) S-烷基二硫代碳酸酯,热解生成2-烯基烷基硫醚(烯丙基硫醚)。该反应遵循一级速率定律,对介质的电离能力相对不敏感,并且活化熵显著为负。当含有不同S-(2-烯基)基团和不同S-烷基基团的两种二硫酯混合物进行热解时,未观察到“交叉产物”。发现反应在酚类化合物或路易斯酸的存在下得到促进。基于这些发现以及改进的原子间重叠忽略(MNDO)计算数据,讨论了2-烯基烷基硫醚生成反应的机理。
  • Retro-ene type fragmentation of allylic dithiolcarbonates
    作者:Masashi Eto、Mitsuhiro Nishimoto、Shoji Kubota、Toshikazu Matsuoka、Kazunobu Harano
    DOI:10.1016/0040-4039(96)00314-0
    日期:1996.4
    The formation of 2-alkenyl alkyl sulfides from S-(2-alkenyl) S-alkyl dithiocarbonates with extrusion of COS was found to be effectively catalyzed by Lewis acids. The ab initio calculations strongly suggested that the reaction falls into category of “retro-alkylthio-ene” reaction.
    发现通过挤出COS由S-(2-链烯基)S-烷基二硫代碳酸酯形成2-链烯基烷基硫化物可有效地被路易斯酸催化。该从头计算强烈建议反应属于“复古硫基烯”反应的范畴。
  • Catalytic behavior of phenols in pyrolytic conversion of allylic dithiolcarbonates to allylic sulfides.
    作者:Kazunobu HARANO、Shigeru YAMASHIRO、Keisuke MISAKA、Takuzo HISANO
    DOI:10.1248/cpb.38.2956
    日期:——
    Pyrolytic conversion of S-(2-alkenyl) S-alkyl dithiocarbonates (allylic dithiolcarbonates) to 2-alkenyl alkyl sulfides (allylic sulfides) was catalyzed by phenols bearing electron-attracting substituents. The reaction is pseudo-first-order and the apparent first-order rate constants are proportional not only to the concentration of phenols but also to the hydrogen-bonding capability of phenols. The entropy of activation for the phenol-catalyzed reaction is ca. 8 e.u. smaller than that for the uncatalyzed reaction. The reactivity of S-(1-phenylallyl) S-alkyl dithiocarbonates did not obey Hammett's or Taft's equation. Based on these findings together with the MNDO (modified neglect of diatomic overlap) calculation data, a possible role of phenols in the pyrolytic conversion of allylic dithiolcarbonates to allylic sulfides is discussed.
    在具有电子吸引取代基的酚类催化下,S-(2-烯基)S-烷基二硫代碳酸盐(烯丙基二硫代碳酸盐)发生热解转化,生成2-烯基烷基硫化物(烯丙基硫化物)。反应呈现伪一级动力学特征,表观一级速率常数不仅与酚类浓度成正比,还与酚类的氢键形成能力成正比。与非催化反应相比,酚类催化反应的活化熵减少了约8熵单位。S-(1-苯基烯丙基)S-烷基二硫代碳酸盐的反应活性不遵循Hammett或Taft方程。结合MNDO(修正的双原子重叠忽略)计算数据,基于这些发现,讨论了酚类在烯丙基二硫代碳酸盐热解转化为烯丙基硫化物过程中的可能作用。
  • Nickel(0) Triethyl Phosphite Complex-Catalyzed Allylic Substitution with Retention of Regio- and Stereochemistry
    作者:Yasutaka Yatsumonji、Yusuke Ishida、Akira Tsubouchi、Takeshi Takeda
    DOI:10.1021/ol702122d
    日期:2007.10.1
    Nickel(0) triethyl phosphite complex-promoted reaction of allylic acetates with thiols produced allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeded with retention of regio- and stereochemistry.
    亚磷酸镍(0)亚磷酸三乙酯络合物促进的乙酸烯丙酯与硫醇的反应生成了烯丙基硫醚,且保留了构型而不发生烯丙基重排。烯丙基乙酸酯与醇和酚的类似反应也进行了区域和立体化学的保留。
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