methyl (R,E)-2-((tert-butylsulfinyl)imino)acetate | 221375-50-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (R,E)-2-((tert-butylsulfinyl)imino)acetate
• 英文别名: methyl (2E)-2-[(R)-tert-butylsulfinyl]iminoacetate
• CAS: 221375-50-4
• 化学式: C₇H₁₃NO₃S
• 分子量: 191.251
• InChiKey: ZNYXZULGRNGSKN-FZKGZDJFSA-N

物化性质

• 沸点：
  284.8±23.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R,E)-2-((tert-butylsulfinyl)imino)acetate 在 {rhodium(acetylacetonate)(cis-cyclooctene)2} lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 Proton Sponge 、 1,2-双(二苯基膦基)苯 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 (S)-2-[(R)-2-(4-Chloro-phenyl)-2-(2-methyl-propane-2-sulfinylamino)-acetylamino]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  芳基硼酸与 N-叔丁亚磺酰基亚氨基酯的铑催化加成不对称合成受保护的芳基甘氨酸

  摘要：

  已经开发了一种将 Rh(I) 催化的芳基硼酸加成到 N-叔丁烷亚磺酰基亚氨基酯的新方法，用于不对称合成芳基甘氨酸衍生物。该方法为各种官能化芳基硼酸提供了高产率 (61-90%) 和非对映选择性 (>98:2)。N-亚磺酰基芳基甘氨酸酯产品是用于进一步转化的多功能中间体，包括选择性去除保护基团、转化为 β-氨基醇以及直接掺入肽中。

  DOI：

  10.1021/ja060529h
• 作为产物：
  描述：

  乙醛酸甲酯 、 (R)-(+)-叔丁基亚磺酰胺 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以33.4%的产率得到methyl (R,E)-2-((tert-butylsulfinyl)imino)acetate
  参考文献：
  名称：

  RAS INHIBITORS

  摘要：

  该披露涉及大环化合物，以及能够抑制Ras蛋白质的药物组合物和蛋白质复合物，以及它们在治疗癌症中的用途。

  公开号：

  US20210130326A1

文献信息

• RAS INHIBITORS
  申请人：Revolution Medicines, Inc.

  公开号：US20210130326A1

  公开（公告）日：2021-05-06

  The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.

  该披露涉及大环化合物，以及能够抑制Ras蛋白质的药物组合物和蛋白质复合物，以及它们在治疗癌症中的用途。
• [EN] COVALENT RAS INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE RAS COVALENTS ET LEURS UTILISATIONS
  申请人：REVOLUTION MEDICINES INC

  公开号：WO2021108683A1

  公开（公告）日：2021-06-03

  The disclosure features compounds, or pharmaceutically acceptable salts thereof, alone and in combination with other therapeutic agents, pharmaceutical compositions, and protein conjugates thereof, capable of modulating biological processes including Ras, and their uses in the treatment of cancers.

  该披露涵盖化合物或其药用盐，单独或与其他治疗剂、药物组合和蛋白共轭物结合在一起，能够调节包括Ras在内的生物过程，并在癌症治疗中的用途。
• Synthesis of Enantiomerically Pure <i>N</i>-<i>tert</i>-Butanesulfinyl Imines (<i>tert</i>-Butanesulfinimines) by the Direct Condensation of <i>tert</i>-Butanesulfinamide with Aldehydes and Ketones
  作者：Guangcheng Liu、Derek A. Cogan、Timothy D. Owens、Tony P. Tang、Jonathan A. Ellman

  DOI：10.1021/jo982059i

  日期：1999.2.1

  Experimental details for the first general methods for the one-step preparation of N-tert-butanesulfinyl imines (tert-butanesulfinimines) (2) from aldehydes and ketones is described. To effect the condensations of tert-butanesulfinamide (1) with aldehydes, the Lewis acidic dehydrating agents MgSO4, CuSO4, or Ti(OEt)(4) are employed. Aldehyde condensations mediated by MgSO4 proceed in high yields (84-96%) when an excess of aldehyde is used. In contrast, only a slight excess of aldehyde (1.1 equiv) relative to tert-butanesulfinamide provides sulfinimines in high yields when the more Lewis acidic dehydrating agent CuSO4 is used. The CuSO4-mediated procedure is effective for a wide range of aldehydes, including sterically demanding aldehydes, such as isobutyraldehyde (90%), and electron-rich aldehydes, such as p-anisaldehyde (81%). The still more Lewis acidic Ti(OEt)(4) and Ti(O-i-Pr)(4) also afford N-tert-butanesulfinyl aldimines from especially unreactive aldehydes, such as pivaldehyde (82%). In addition, Ti(OEt)(4) is effective for the condensation of I with ketones to afford a wide range of N-tert-butanesulfinyl ketimines in good yields (77-91%). For sulfinyl ketimines derived from methyl or n-alkyl phenyl ketones and methyl or n-alkyl isopropyl ketones, only the E isomer is detected by H-1 and C-13 NMR in CDCl3. For those cases where the difference in steric demand about the imine is very small, such as for 2-hexanone, high E/Z ratios are still observed (5:1).
• Asymmetric Synthesis of Protected Arylglycines by Rhodium-Catalyzed Addition of Arylboronic Acids to <i>N</i>-<i>tert</i>-Butanesulfinyl Imino Esters
  作者：Melissa A. Beenen、Daniel J. Weix、Jonathan A. Ellman

  DOI：10.1021/ja060529h

  日期：2006.5.1

  the Rh(I)-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters has been developed for the asymmetric synthesis of arylglycine derivatives. This method provides high yields (61-90%) and diastereoselectivities (>98:2) for a variety of functionalized arylboronic acids. The N-sulfinyl arylglycine ester products are versatile intermediates for further transformations, including

  已经开发了一种将 Rh(I) 催化的芳基硼酸加成到 N-叔丁烷亚磺酰基亚氨基酯的新方法，用于不对称合成芳基甘氨酸衍生物。该方法为各种官能化芳基硼酸提供了高产率 (61-90%) 和非对映选择性 (>98:2)。N-亚磺酰基芳基甘氨酸酯产品是用于进一步转化的多功能中间体，包括选择性去除保护基团、转化为 β-氨基醇以及直接掺入肽中。