3-丙-2-基-1,2-苯并噻唑1,1-二氧化物 | 84108-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 3-丙-2-基-1,2-苯并噻唑1,1-二氧化物
• 英文名称: 3-isopropylbenzo[d]isothiazole 1,1-dioxide
• 英文别名: 3-(Propan-2-yl)-1H-1lambda~6~,2-benzothiazole-1,1-dione；3-propan-2-yl-1,2-benzothiazole 1,1-dioxide
• CAS: 84108-97-4
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: CDYWBHRGEXHUPT-UHFFFAOYSA-N

物化性质

• 沸点：
  362.2±25.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-丙-2-基-1,2-苯并噻唑1,1-二氧化物 在 C₄₀H₄₄IrN₆⁽¹⁺⁾*F₆P^(1-) 、 甲酸铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Isopropyl-1,2-benzisothiazoline 1,1-Dioxide
  参考文献：
  名称：

  一种以金属为中心手性的亚胺N-杂环碳铱铱催化剂，用于亚胺的对映选择性转移加氢

  摘要：

  设计了具有金属中心手性的环金属化N-杂环卡宾铱配合物，并将其应用于亚胺的不对称转移氢化（ATH）。四个强σ供电的碳基取代基（2个碳烯和2个苯基部分），手性直接从立体金属中心转移至底物的C = N键，以及由于空间要求的取代基限制了催化剂的失活就催化剂的负载量（低至0.01 mol％），底物范围（24个实例）和对映选择性（94-98％ee）而言，这种新型的络合物是用于环N-磺酰亚胺的ATH的最有效的催化剂之一。

  DOI：

  10.1039/c7cc04691j
• 作为产物：
  描述：

  邻氯苯磺酰胺 在 正丁基锂 、 sodium hydride 作用下， 反应 5.5h， 生成 3-丙-2-基-1,2-苯并噻唑1,1-二氧化物
  参考文献：
  名称：

  Aromatic heteroannulation via metalation-cyclization of N-acyl-2-chlorobenzenesulfonamides and N-acylbenzenesulfonamides

  摘要：

  N-Acyl-2-chlorobenzenesulfonamides 7a-d undergo competitive metal-halogen exchange and or alpha-deprotonation reactions when treated sequentially with sodium hydride and n-butyllithium. The o-lithio intermediates derived from metal-halogen exchange and ortho-deprotonation undergo cyclization to afford 3-substituted 1,2-benzisothiazole 1,1-dioxides 10a-d and 3-substituted 7-chloro-1,2-benzisothiazole 1,1-dioxides 14a-d, respectively. Reaction time-temperature data show evidence for the slow conversion of the lateral dianion of N-acetyl-2-chlorobenzenesulfonamide (7a) to the corresponding N,ortho-dialkali salt. 1,2-Benzisothiazole 1,1-dioxides 14a-d were obtained in good yield and free from products resulting from metal-halogen exchange by treatment of sulfonamides 7a-d with 2 equiv of LDA in THF. In the presence of 2 equiv of LDA, N-acylbenzenesulfonamides devoid of or containing only weakly acidic alpha-hydrogens undergo alpha-deprotonation-cyclization to afford the respective 1,2-benzoisothiazole 1,1-dioxides.

  DOI：

  10.1021/jo00046a012

文献信息

• Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines
  作者：Jose I. Martínez、Joshua J. Smith、Hamish B. Hepburn、Hon Wai Lam

  DOI：10.1002/anie.201508964

  日期：2016.1.18

  Allylrhodium species derived from δ‐trifluoroboryl β,γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z‐alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the

  衍生自 δ-三氟硼基 β,γ-不饱和酯的烯丙基铑物种向酯部分进行链式行走。所得的烯丙基铑物质与亚胺反应，得到含有两个新立体中心和一个Z-烯烃的产物。通过使用手性二烯配体，可以获得具有高对映选择性的产品，其中与烯丙基三氟硼酸酯的手性的明显匹配/错配效应是明显的。
• A Palladium-Catalyzed Enantioselective Addition of Arylboronic Acids to Cyclic Ketimines
  作者：Guoqiang Yang、Wanbin Zhang

  DOI：10.1002/anie.201302861

  日期：2013.7.15

  Nicox: A palladium‐catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α‐tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA=trifluoroacetate.

  像Nicox一样狡猾：已开发出一种钯催化的芳基硼酸加成酮亚胺，以有效地提供高达99％的收率和96％ee的产品。反应可以在有氧条件下和未纯化的三氟乙醇（TFE）下进行。几步合成了带有手性α-叔胺的吡咯烷化合物，且不损失对映选择性。TFA ＝三氟乙酸盐。
• Rhodium-Catalyzed Asymmetric Arylation of Cyclic <i>N</i>-Sulfonyl Aryl Alkyl Ketimines: Efficient Access to Highly Enantioenriched α-Tertiary Amines
  作者：Tao Jiang、Zheng Wang、Ming-Hua Xu

  DOI：10.1021/ol503537w

  日期：2015.2.6

  A simple catalyst system of Rh(I)/sulfur-olefin with exceptional catalytic performance has been developed for the highly enantioselective arylation of cyclic N-sulfonyl aryl alkyl ketimines with arylboroxines/arylboronic acids. Optically active α-arylalkyl-substituted benzosultams and benzosulfamidates which are generally difficult to obtain were easily prepared with excellent stereocontrol (up to

  已经开发了具有优异催化性能的Rh（I）/硫-烯烃的简单催化剂体系，用于环状N-磺酰基芳基烷基酮亚胺与芳基硼氧烷/芳基硼酸的高度对映选择性芳基化。通常难以获得的旋光性α-芳基烷基取代的苯并阿磺酸和苯甲磺酰胺，很容易以优异的立体控制（高达99.9％ee）进行制备。NMDA拮抗剂FR115427和苯并恶嗪酮衍生物的简便构建证明了该方法的综合实用性。该方案为有效合成各种手性α-叔胺提供了新的机会。
• The evaluation of chiral benzosultams as auxiliaries in asymmetric azidation reaction
  作者：Kyo Han Ahn、Seung-Ki Kim、Chul Ham

  DOI：10.1016/s0040-4039(98)01341-0

  日期：1998.8

  Several chiral 3-substituted benzosultams, synthesized through an enantioselective Ru(II)-catalyzed transfer hydrogenation of corresponding sulfonylimines, are evaluated as chiral auxiliaries in the asymmetric azidation reaction of their N-acyl derivatives. π-Facial selectivities of up to 99:1 are observed.

  在对映体的N-酰基衍生物的不对称叠氮化反应中，通过对映选择性Ru（II）催化对映体磺酰亚胺的转移氢化合成的几种手性3-取代的苯并合苯胺被评价为手性助剂。观察到高达99：1的π面选择性。
• Compounds Useful In Therapy
  申请人：Bryans Justin Stephen

  公开号：US20080188478A1

  公开（公告）日：2008-08-07

  Compounds of formula (I), or pharmaceutically acceptable derivatives thereof, wherein: R 1 represents a group selected from H, CF 3 , and C 1-6 alkyl (optionally substituted by C 1-6 alkyloxy or triazolyl); R 2 represents halo; Ring A represents a 5- or 6-membered heterocyclic ring containing at least one N atom (the ring being optionally bridged with two or more carbon atoms); R 3 represents a 5- or 6-membered heterocyclic ring containing at least one atom selected from N, O or S, the heterocyclic ring being optionally substituted by one or more groups selected from C 1-6 alkyl oxo or NH 2 , the heterocyclic ring being further optionally fused to a 5- or 6-membered aryl or heterocyclic ring containing at least one atom selected from N, O or S, the fused aryl or heterocyclic ring being substituted by one or more halo atoms; are useful for treating a disorder for which a V1a antagonist is indicated, in particular, dysmenorrhea.

  式(I)的化合物或其药学上可接受的衍生物，其中： R1表示从H，CF3和C1-6烷基（可选地被C1-6烷氧基或三唑基取代）中选择的基团； R2表示卤素； 环A表示含有至少一个N原子的5-或6成员杂环，（该环可与两个或更多个碳原子桥接）； R3表示含有至少一个从N，O或S中选择的原子的5-或6成员杂环，该杂环可被选自C1-6烷基氧或NH2的一个或多个基团取代，该杂环进一步可融合到一个含有至少一个从N，O或S中选择的原子的5-或6成员芳香族或杂环中，该融合的芳香族或杂环被一个或多个卤素原子取代； 用于治疗需要V1a拮抗剂的疾病，特别是痛经。