(R)-(-)-1-(1-萘基)异硫氰酸乙酯 | 138617-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (R)-(-)-1-(1-萘基)异硫氰酸乙酯
• 中文别名: (R)-(-)-1-(1-萘基)乙基硫代异氰酸酯
• 英文名称: (R)-[1-(1-naphthyl)ethyl] isothiocyanate
• 英文别名: 1-[(R)-1-isothiocyanatoethyl]naphthalene；(1R)-1-(1-naphthyl)ethyl isothiocyanate；(R)-1-(1-naphthyl)ethylisothiocyanate；(R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate；1-[(1R)-1-isothiocyanatoethyl]naphthalene
• CAS: 138617-82-0
• 化学式: C₁₃H₁₁NS
• 分子量: 213.303
• InChiKey: PGJWLIIUEIYCSF-SNVBAGLBSA-N

物化性质

• 密度：
  1,155 g/cm3
• 稳定性/保质期：
  如果按照规格使用和储存，不会发生分解，也无已知危险反应。应避免与氧化物、水分等接触。

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2930909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 2810

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
  (R)-1-(1-萘基)乙胺	(R)-1-(1-Naphthyl)ethylamine	3886-70-2	C12H13N	171.242

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-(1-萘基)异硫氰酸乙酯 在 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 102.0h， 生成 (4S,5S)-4,5-diphenyl-2-[(R)-1-(1-naphthyl)ethylimino]imidazolidine
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n
• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 在 2-氯-1,3-二甲基氯化咪唑啉 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-(-)-1-(1-萘基)异硫氰酸乙酯
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n

文献信息

• Chiral thiourea compounds and process for enantioselective reduction of ketones
  申请人：Li Derun

  公开号：US20090253919A1

  公开（公告）日：2009-10-08

  Chiral thioureas are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols. A prochiral ketone may be reduced to an optically active alcohol in the presence of a substantially sub-stoichiometric amount of chiral thiourea. The asymmetric thiourea compound of the present invention may be produced according to a production method described herein.

  手性硫脲是对丙酮进行硼氢化还原生成光学活性醇的有效催化剂。在存在明显亚化学计量量手性硫脲的情况下，可以将一个丙酮还原为光学活性醇。本发明的不对称硫脲化合物可以根据本文描述的生产方法制备。
• A Simple Organocatalytic Enantioselective Synthesis of Pregabalin
  作者：Oriol Bassas、Juhani Huuskonen、Kari Rissanen、Ari M. P. Koskinen

  DOI：10.1002/ejoc.200801220

  日期：2009.3

  synthetic sequence is the Michael addition reaction of Meldrum's acid to a nitroalkene mediated by a quinidine derived thiourea. A variety of novel catalysts bearing different groups at the thiourea moiety were synthesized and tested. The most successful catalyst that incorporates a trityl substituent provided up to 75 % ee of (S)-4. The conjugate addition reaction was carried out on a multigram scale

  本文介绍了一种对映选择性合成重要的抗惊厥药物普瑞巴林的新方法，该方法仅显示 (S) 对映异构体的生物学特性。合成序列的关键步骤是由奎尼丁衍生的硫脲介导的 Meldrum 酸与硝基烯烃的迈克尔加成反应。合成并测试了多种在硫脲部分带有不同基团的新型催化剂。掺入三苯甲基取代基的最成功的催化剂提供高达 75% ee 的 (S)-4。共轭加成反应以多克规模进行，催化剂负载量低（10 mol%）。此外，催化剂可以循环使用，在化学产率和不对称诱导方面表现出相同的能力。然后，硝基烷烃 4 氢化，然后二酸 5 脱羧，得到普瑞巴林盐酸盐，总产率为 59%。通过游离氨基酸 1 结晶的对映体富集将 (S)/(R) 对映体比例提高到 9:1。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• (<i>R</i>)-[1-(1-Naphthyl)ethyl] Isothiocyanate and (<i>S</i>)-1-Phenylethyl Isothiocyanate. New Chirality Recognizing Reagents for the Determination of Enantiomeric Purity of Chiral Amines by NMR
  作者：Dong Ju Jeon、Jung Soo Kim、Jung No Lee、Hyoung Rae Kim、Eung K. Ryu

  DOI：10.1246/cl.2000.40

  日期：2000.1

  (S)-1-Phenylethyl isothiocyanate and (R)-[1-(1-naphthyl)ethyl] isothiocyanate which are easily formed and stable in aqueous conditions are utilized as new chirality recognizing reagents for the determination of enantiomeric purity of chiral amines by NMR.

  (S)-1-苯基乙基异硫氰酸酯和(R)-[1-(1-萘基)乙基]异硫氰酸酯在水性条件下易于形成且稳定，被用作新的手性识别试剂，用于测定手性胺的对映体纯度核磁共振。
• Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea–amine bifunctional organocatalysts
  作者：Svetlana B. Tsogoeva、Shengwei Wei

  DOI：10.1039/b517937h

  日期：——

  and effective organocatalytic system: primary amine derived chiral thiourea catalyst and AcOH-H2O additive, which converts different ketones to gamma-nitroketones in high yields (82-99%) and enantioselectivities (90-99%) has been described.

  已经描述了一种新的有效的有机催化体系：伯胺衍生的手性硫脲催化剂和AcOH-H2O添加剂，该体系可将不同的酮以高收率（82-99％）和对映选择性（90-99％）转化为γ-硝基酮。
• Crystallographic, 1H NMR and CD studies of sterically strained thiourea anion receptors possessing two stereogenic centres
  作者：Haslin Dato Paduka Ali、Susan J. Quinn、Thomas McCabe、Paul E. Kruger、Thorfinnur Gunnlaugsson

  DOI：10.1039/b819638a

  日期：——

  three chiral bis-naphthalene thiourea receptors (1–3) derived from (R)-(+)-1-(1-naphthyl)ethylamine and (S)-(−)-1-(1-naphthyl)ethylamine are reported along with spectroscopic studies to screen their potential as anion receptors/sensors. Their solid state structures were analysed by X-ray crystallography and their ability to bind anions such as acetate and phosphate in DMSO solution investigated by 1H

  三种衍生自手性的双萘硫脲受体（1-3）的合成和结构表征（R）-（+）-1-（1-萘基）乙胺 和 （S）-（-）-1-（1-萘基）乙胺与光谱研究一起被报道以筛选其作为阴离子受体/传感器的潜力。通过X射线晶体学分析它们的固态结构，并通过1 H NMR，吸收，荧光和圆二色谱法研究它们在DMSO溶液中与阴离子如乙酸根和磷酸根结合的能力。