3-benzyl-4,4-dimethyl-[1,2,3]-oxathiazolidine-2,2-dioxide | 228547-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyl-4,4-dimethyl-[1,2,3]-oxathiazolidine-2,2-dioxide
• 英文别名: 3-benzyl-4,4-dimethyl-1,2,3-oxathiazolidine 2,2-dioxide；3-benzyl-4,4-dimethyl-1,2,3-oxathiazole-2,2-dioxide；3-benzyl-4,4-dimethyl-1,2,3-oxathiazolidine-2,2-dioxide；3-benzyl-4,4-dimethyl-1,2,3-oxathiazole-2-dioxide；1,2,3-Oxathiazolidine, 4,4-dimethyl-3-(phenylmethyl)-, 2,2-dioxide；3-benzyl-4,4-dimethyloxathiazolidine 2,2-dioxide
• CAS: 228547-64-6
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: NEECDVMYLJIKPB-UHFFFAOYSA-N

物化性质

• 沸点：
  344.3±35.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-4,4-dimethyl-[1,2,3]-oxathiazolidine-2,2-dioxide 在 二甲醇缩甲醛 、 caesium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.0h， 生成 5-benzyl-3-bromo-6,6-dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine
  参考文献：
  名称：

  Structure-Based Drug Design of Novel Potent and Selective Tetrahydropyrazolo[1,5-a]pyrazines as ATR Inhibitors

  摘要：

  A saturation strategy focused on improving the selectivity and physicochemical properties of ATR inhibitor HTS hit 1 led to a novel series of highly potent and selective tetrahydropyrazolo[1,5-a]pyrazines. Use of PI3K alpha mutants as ATR crystal structure surrogates was instrumental in providing cocrystal structures to guide the medicinal chemistry designs. Detailed DMPK studies involving cyanide and GSH as trapping agents during microsomal incubations, in addition to deuterium-labeled compounds as mechanistic probes uncovered the molecular basis for the observed CYP3A4 TDI in the series.

  DOI：

  10.1021/ml500353p
• 作为产物：
  描述：

  3-benzyl-4,4-dimethyl-1,2,3-oxathiazole-2-oxide 在 ruthenium trichloride 、 sodium periodate 作用下， 以 水 、 乙腈 为溶剂， 生成 3-benzyl-4,4-dimethyl-[1,2,3]-oxathiazolidine-2,2-dioxide
  参考文献：
  名称：

  β-氨基二硫化物、胱氨酸的简便合成及其直接掺入肽

  摘要：

  在此，我们报告了一种简单有效的方法，用于通过磺酰胺与四硫代钼酸苄基三乙基铵 [BnNEt3](2)MoS4 的区域选择性开环来合成 β-氨基二硫化物。讨论了不同保护基在反应条件下的稳定性和反应性。这种方法也已扩展到丝氨酸和苏氨酸衍生的磺酰胺以提供胱氨酸和 3,3'-二甲基胱氨酸衍生物。

  DOI：

  10.1055/s-0028-1088133

文献信息

• One-pot synthesis of functionalized β-amino sulfides/β-amino selenides via ring opening of cyclic sulfamidates
  作者：Cheerladinne Venkateswarlu、Bandita Datta、Srinivasan Chandrasekaran

  DOI：10.1039/c4ra06759b

  日期：——

  A number of functionalized β-amino and γ-amino sulfides and selenides have been synthesized involving a one-pot process of ring opening of cyclic sulfamidates with ‘in situ’ generated thiolate and selenoate species from diaryl disulfides and diphenyl diselenide using rongalite. A mild and efficient method has been developed for the synthesis of cysteines from serine.

  已经合成了许多功能化的β-氨基和γ-氨基硫化物和硒化物，涉及一锅法将环状氨基磺酸盐与二芳基二硫化物和二苯基二硒化物使用白锌矿“原位”生成的硫醇盐和硒酸酯物种一起开环。已经开发了一种温和而有效的方法，用于从丝氨酸合成半胱氨酸。
• New Routes to N-Alkylated Cyclic Sulfamidates
  作者：Jeffrey J. Posakony、John R. Grierson、Timothy J. Tewson

  DOI：10.1021/jo0157019

  日期：2002.7.1

  BOC- and dibenzosuberyl-protected chiral and hindered cyclic sulfamidates ([1,2,3]-oxathiazolidine-2,2-dioxides) were synthesized and subsequently deprotected using trifluoroacetic acid. The resulting crystalline sulfamidates were then used in several alkylation reactions involving benzyl bromide and alcohols in a versatile route to cyclic sulfamidates with differing N-alkyl substituents.

  合成了BOC和二苯并亚戊基保护的手性和受阻的环氨基磺酸盐（[1,2,3]-氧代噻唑烷-2,2-二氧化物），然后使用三氟乙酸脱保护。然后将所得的结晶氨基磺酸盐用于涉及苄基溴和醇的几种烷基化反应中，以通用的方式合成具有不同N-烷基取代基的环状氨基磺酸盐。
• Substitution Reactions of Hindered Cyclic Sulfamidates
  作者：Jeffrey J. Posakony、Timothy J. Tewson

  DOI：10.1055/s-2002-28509

  日期：——

  Five- and six-membered cyclic sulfamidates, [1,2,3]-oxathiazolidine- and [1,2,3]-oxathiazinane-2,2-dioxides, with the leaving group oxygen at sterically hindered centers were synthesized and treated with selected nucleophiles (azide, cyanide, fluoride, butylamine, sec-butylamine, tert-amylamine, and imidazole) in substitution reactions to demonstrate the general utility and limitations of these substrates. Substitutions adjacent to quaternary carbon centers were accomplished with relative ease. In contrast to the 4,4-dimethyl substituted 5-membered sulfamidate 1, which reacted with the entire set of nucleophiles, the more hindered 5-membered and 6-membered sulfamidates (7 and 6, respectively) reacted only with the first few of this set.

  我们合成了五元和六元环状氨基磺酸盐、[1,2,3]-氧硫杂唑烷和[1,2,3]-氧硫杂嗪烷-2,2-二氧化物，其离去基团氧位于立体受阻中心，并在取代反应中与选定的亲核物（叠氮化物、氰化物、氟化物、丁胺、仲丁胺、叔胺和咪唑）进行了处理，以证明这些底物的一般用途和局限性。邻近季碳中心的取代反应相对容易完成。与 4,4-二甲基取代的 5 元氨基磺酸盐 1 与整组亲核物发生反应不同，受阻较大的 5 元和 6 元氨基磺酸盐（分别为 7 元和 6 元）只与这组亲核物中的前几种发生反应。
• Amidopyrazole Derivative
  申请人：Kanaya Naoaki

  公开号：US20070219210A1

  公开（公告）日：2007-09-20

  A platelet coagulation inhibitor which inhibits neither COX-1 nor COX-2 is provided. The inhibitor is a compound represented by general formula (I): wherein Ar 1 and Ar 2 independently represent a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents, or a phenyl group optionally substituted with 1 to 3 substituents; R1 represents a lower acyl group, carboxyl group, a lower alkoxy carbonyl group, a lower alkoxy group, a lower alkyl group optionally substituted with 1 or 2 substituents, a carbamoyl group optionally substituted with 1 or 2 substituents, an oxamoyl group optionally substituted with 1 or 2 substituents, an amino group optionally substituted with 1 or 2 substituents, a 4- to 7-membered alicyclic heterocyclic group optionally substituted with 1 or 2 substituents, a phenyl group optionally substituted with 1 to 3 substituents, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents; and R2 represents hydrogen atom, a halogeno group, or the like.

  提供了一种血小板凝血抑制剂，它既不抑制COX-1也不抑制COX-2。该抑制剂是由通式（I）表示的化合物：其中Ar1和Ar2独立地表示一个5-或6-成员的芳香杂环基团，可选地取代1至3个取代基，或一个苯基，可选地取代1至3个取代基；R1表示较低的酰基，羧基，较低的烷氧羰基，较低的烷氧基，较低的烷基，可选地取代1或2个取代基的氨基甲酰基，可选地取代1或2个取代基的草酰基，可选地取代1或2个取代基的氧代草酰基，可选地取代1或2个取代基的氨基，可选地取代1或2个取代基的4-至7-成员脂环杂环基团，可选地取代1或2个取代基的苯基，或可选地取代1至3个取代基的5-或6-成员芳香杂环基团；R2表示氢原子，卤素基或类似物。
• AMIDOPYRAZOLE DERIVATIVE
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1698626A1

  公开（公告）日：2006-09-06

  A platelet coagulation inhibitor which inhibits neither COX-1 nor COX-2 is provided. The inhibitor is a compound represented by general formula (I): wherein Ar1 and Ar2 independently represent a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents, or a phenyl group optionally substituted with 1 to 3 substituents; R1 represents a lower acyl group, carboxyl group, a lower alkoxycarbonyl group, a lower alkoxy group, a lower alkyl group optionally substituted with 1 or 2 substituents, a carbamoyl group optionally substituted with 1 or 2 substituents, an oxamoyl group optionally substituted with 1 or 2 substituents, an amino group optionally substituted with 1 or 2 substituents, a 4- to 7-membered alicyclic heterocyclic group optionally substituted with 1 or 2 substituents, a phenyl group optionally substituted with 1 to 3 substituents, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents; and R2 represents hydrogen atom, a halogeno group, or the like.

  提供了一种既不抑制 COX-1 也不抑制 COX-2 的血小板凝固抑制剂。该抑制剂为通式 (I) 所代表的化合物： 其中 Ar1 和 Ar2 独立地代表任选被 1 至 3 个取代基取代的 5 或 6 元芳香杂环基团，或任选被 1 至 3 个取代基取代的苯基；R1 代表低级酰基、羧基、低级烷氧羰基、低级烷氧基、任选被 1 或 2 个取代基取代的低级烷基、任选被 1 或 2 个取代基取代的氨基甲酰基、任选被 1 或 2 个取代基取代的草酰基、任选被 1 或 2 个取代基取代的氨基，任选被 1 或 2 个取代基取代的 4 至 7 元脂环杂环基团，任选被 1 至 3 个取代基取代的苯基，或任选被 1 至 3 个取代基取代的 5 或 6 元芳香杂环基团；R2 代表氢原子、卤素基团或类似物。