(S)-2-(1-Chloro-2-methyl-2-propanyl)-4-isopropyl-4,5-dihydrooxazole | 1199225-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (S)-2-(1-Chloro-2-methyl-2-propanyl)-4-isopropyl-4,5-dihydrooxazole
• 英文别名: (4S)-2-(1-chloro-2-methylpropan-2-yl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 1199225-39-2
• 化学式: C₁₀H₁₈ClNO
• 分子量: 203.712
• InChiKey: KKZCAJJMWXCQPL-MRVPVSSYSA-N

物化性质

• 密度：
  1.009 g/mL at 25 °C
• 闪点：
  93℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(1-Chloro-2-methyl-2-propanyl)-4-isopropyl-4,5-dihydrooxazole 、 potassium diphenylphosphine 以 四氢呋喃 为溶剂， 反应 6.0h， 以92%的产率得到(S)-2-(1-(diphenylphosphaneyl)-2-methylpropan-2-yl)-4-isopropyl-4,5-dihydrooxazole
  参考文献：
  名称：

  NeoPHOX-用于不对称催化的结构可调的配体系统。

  摘要：

  已开发出衍生自丝氨酸或苏氨酸的新NeoPHOX配体的合成。中心中间体是在紧靠恶唑啉N原子的立体异构中心带有甲氧基羰基的NeoPHOX衍生物。甲基氯化镁的加入产生了叔醇，其可以被酰化或甲硅烷基化以产生具有不同空间需求的NeoPHOX配体。在铱催化的不对称氢化和钯催化的烯丙基取代中测试了新的NeoPHOX配体。在这两个反应中，都实现了高对映选择性，这与使用目前为止从昂贵的叔亮氨酸衍生的最新最好的NeoPHOX配体所获得的对映选择性相当。

  DOI：

  10.3762/bjoc.12.114
• 作为产物：
  描述：

  氯代特戊酰氯 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-2-(1-Chloro-2-methyl-2-propanyl)-4-isopropyl-4,5-dihydrooxazole
  参考文献：
  名称：

  NeoPHOX-用于不对称催化的结构可调的配体系统。

  摘要：

  已开发出衍生自丝氨酸或苏氨酸的新NeoPHOX配体的合成。中心中间体是在紧靠恶唑啉N原子的立体异构中心带有甲氧基羰基的NeoPHOX衍生物。甲基氯化镁的加入产生了叔醇，其可以被酰化或甲硅烷基化以产生具有不同空间需求的NeoPHOX配体。在铱催化的不对称氢化和钯催化的烯丙基取代中测试了新的NeoPHOX配体。在这两个反应中，都实现了高对映选择性，这与使用目前为止从昂贵的叔亮氨酸衍生的最新最好的NeoPHOX配体所获得的对映选择性相当。

  DOI：

  10.3762/bjoc.12.114

文献信息

• NeoPHOX—an easily accessible P,N-ligand for iridium-catalyzed asymmetric hydrogenation: preparation, scope and application in the synthesis of demethyl methoxycalamenene
  作者：Marcus G. Schrems、Andreas Pfaltz

  DOI：10.1039/b912680e

  日期：——

  Using a new class of chiral iridium hydrogenation catalysts, the antitumor natural product demethyl calamenene was synthesized in four steps in >20% overall yield and high enantiomeric purity.

  采用新型手性铱氢化催化剂，抗肿瘤天然产物去甲基石竹烯经四步合成，总产率超过20%，且具有高度的手性纯度。
• Chiral ligands
  申请人：Solvias AG

  公开号：EP2202236A1

  公开（公告）日：2010-06-30

  Chiral compounds of the formula (1), which are optically pure or highly optically enriched in which R0 is C1-C12-alkyl which is unsubstituted or substituted by 1 to 2 C1-C4-alkoxy; cyclopentyl or cyclohexyl, which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl or C1-C4-alkoxy; or benzyl, phenyl or naphtyl which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl or C1-C4-fluoroalkoxy, F or Cl, each of R1 and R'1 independently is hydrogen or has the meaning of R0 whereby R1, R'1 and R0 can be same or different, R2 and R3 are independently a C-bonded hydrocarbon radical or a heterohydrocarbon radical, and each of both R4 is C1-C6-alkyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, methylbenzyl or benzyl, or both R4 together form an aliphatic C4-C6 carbocycle. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reaction, particularly hydrogenations.

  化学式（1）的手性化合物，其光学纯度高或光学富集，其中R0是未取代或取代1至2个C1-C4-烷氧基的C1-C12-烷基；环戊基或环己基，未取代或取代1至3个C1-C4-烷基或C1-C4-烷氧基；或苄基，苯基或萘基，未取代或取代1至3个C1-C4-烷基，C1-C4-烷氧基，C1-C4-氟烷基或C1-C4-氟烷氧基，F或Cl，R1和R'1中的每一个独立地是氢或具有R0的含义，其中R1，R'1和R0可以相同也可以不同，R2和R3独立地是C键合的碳氢基团或杂原子碳氢基团，R4中的每一个都是C1-C6-烷基，环戊基，环己基，苯基，甲基苯基，甲基苄基或苄基，或者两个R4一起形成一个脂肪族C4-C6碳环。这些配体的金属络合物是对不对称加成反应，尤其是氢化反应的均相催化剂。
• CHIRAL LIGANDS
  申请人：Pfaltz Andreas

  公开号：US20110275826A1

  公开（公告）日：2011-11-10

  Chiral compounds of the formula (1), which are optically pure or highly optically enriched in which R 0 is C 1 -C 12 -alkyl which is unsubstituted or substituted by 1 to 2 C 1 -C 4 -alkoxy; cyclo-pentyl or cyclohexyl, which is unsubstituted or substituted by 1 to 3 C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; or benzyl, phenyl or naphtyl which is unsubstituted or substituted by 1 to 3 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl or C 1 -C 4 -fluoroalkoxy, F or Cl, or R 0 is —CR 5 R 6 OH or —CR 5 R 6 OSi(C 1 -C 8 -alkyl) 3 wherein R 5 and R 6 are independently selected from the group consisting of H, unsubstituted C 1 -C 12 alkyl, substituted C 1 -C 12 alkyl, unsubstituted C 4 -C 8 cyclo alkyl, substituted C 4 -C 8 cyclo alkyl, unsubstituted aryl, substituted aryl or wherein R 5 and R 6 can form an unsubstituted 5-6 membered aliphatic carbocycle or a substituted 5-6 membered aliphatic carbocycle, each of R 1 and R′ 1 independently is hydrogen or has the meaning of R 0 whereby R 1 , R′ 1 and R 0 can be same or different, R 2 and R 3 are independently a C-bonded hydrocarbon radical or a heterohydrocarbon radical, and each of both R 4 is C 1 -C 6 -alkyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, methylbenzyl or benzyl, or both R 4 together form an aliphatic C 4 -C 6 carbocycle. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reaction, particularly hydrogenations.
• [EN] CHIRAL LIGANDS<br/>[FR] LIGANDS CHIRAUX
  申请人：SOLVIAS AG

  公开号：WO2010072746A1

  公开（公告）日：2010-07-01

  Chiral compounds of the formula (1 ), which are optically pure or highly optically enriched in which R0 is C1-C12-alkyl which is unsubstituted or substituted by 1 to 2 C1-C4-alkoxy; cyclo- pentyl or cyclohexyl, which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl or C1-C4-alkoxy; or benzyl, phenyl or naphtyl which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl or C1-C4-fluoroalkoxy, F or Cl, or R0 is -C R5 R6 OH or -C R5 R6 OSi(C1-C8-alkyl)3 wherein R5 and R6 are indedendently selected from the group consisting of H, unsubstituted C1 - C12 alkyl, substituted C1 - C12 alkyl, unsubstituted C4 - C8 cyclo alkyl, substituted C4 - C8 cyclo alkyl, unsubstituted aryl, substituted aryl or wherein R5 and R6 can form an unsubstituted 5-6 membered aliphatic carbocycle or a substituted 5-6 membered aliphatic carbocycle, each of R1 and R'1 independently is hydrogen or has the meaning of R0 whereby R1, R'1 and R0 can be same or different, R2 and R3 are independently a C-bonded hydrocarbon radical or a heterohydrocarbon radical, and each of both R4 is C1-C6-alkyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, methylbenzyl or benzyl, or both R4 together form an aliphatic C4-C6 carbocycle. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reaction, particularly hydrogenations.
• NeoPHOX – a structurally tunable ligand system for asymmetric catalysis
  作者：Jaroslav Padevět、Marcus G Schrems、Robin Scheil、Andreas Pfaltz

  DOI：10.3762/bjoc.12.114

  日期：——

  A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central intermediate is a NeoPHOX derivative bearing a methoxycarbonyl group at the stereogenic center next to the oxazoline N atom. The addition of methylmagnesium chloride leads to a tertiary alcohol, which can be acylated or silylated to produce NeoPHOX ligands with different sterical demand. The new NeoPHOX

  已开发出衍生自丝氨酸或苏氨酸的新NeoPHOX配体的合成。中心中间体是在紧靠恶唑啉N原子的立体异构中心带有甲氧基羰基的NeoPHOX衍生物。甲基氯化镁的加入产生了叔醇，其可以被酰化或甲硅烷基化以产生具有不同空间需求的NeoPHOX配体。在铱催化的不对称氢化和钯催化的烯丙基取代中测试了新的NeoPHOX配体。在这两个反应中，都实现了高对映选择性，这与使用目前为止从昂贵的叔亮氨酸衍生的最新最好的NeoPHOX配体所获得的对映选择性相当。