methyl 3-aminopropyl sulfoxide | 196200-06-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: methyl 3-aminopropyl sulfoxide
• 英文别名: 3-(methylsufinyl)propan-1-amine；3-(methylsulfinyl)propylamine；(+)-(S)-3-Methylsulfinyl-propylamin；rac.-3-Methylsulfinyl-propylamin；(S)-3-methanesulfinyl-propylamine；(S)-3-Methansulfinyl-propylamin；(+/-)-3-methanesulfinyl-propylamine；(+/-)-3-Methansulfinyl-propylamin；3-Methylsulfoxido-propylamin；Methyl-(γ-amino-propyl)-sulfoxyd；3-Methanesulfinylpropan-1-amine；3-methylsulfinylpropan-1-amine
• CAS: 196200-06-3
• 化学式: C₄H₁₁NOS
• mdl: MFCD14612914
• 分子量: 121.203
• InChiKey: COPMQUUNXNNQJO-UHFFFAOYSA-N

物化性质

• 熔点：
  27 °C
• 沸点：
  90-91 °C(Press: 0.04 Torr)
• 密度：
  1.124±0.06 g/cm3(Predicted)
• 溶解度：
  二氯甲烷（少量溶解）、甲醇（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  methyl 3-aminopropyl sulfoxide 生成 3-甲基亚磺酰丙基异硫氰酸酯
  参考文献：
  名称：

  关于萝卜硫烷的同系物和ω-氨基烷基亚砜

  摘要：

  已经以外消旋和旋光形式制备了萝卜硫烷的较高和较低的同系物。合成的化合物如下：

  DOI：

  10.1002/hlca.19500330516
• 作为产物：
  描述：

  3-(甲基三)丙烯酸呋喃 在 双氧水 、 丙酮 作用下， 生成 methyl 3-aminopropyl sulfoxide
  参考文献：
  名称：

  关于萝卜硫烷的同系物和ω-氨基烷基亚砜

  摘要：

  已经以外消旋和旋光形式制备了萝卜硫烷的较高和较低的同系物。合成的化合物如下：

  DOI：

  10.1002/hlca.19500330516

文献信息

• Analysis and Anti-Helicobacter Activity of Sulforaphane and Related Compounds Present in Broccoli (Brassica oleracea L.) Sprouts
  作者：Joon-Kwan Moon、Jun-Ran Kim、Young-Joon Ahn、Takayuki Shibamoto

  DOI：10.1021/jf1003573

  日期：2010.6.9

  sulforaphane-related compounds were positively identified in the chloroform extract, of which 5-methylsulfinylpentylnitrile was found in the greatest concentration (475.7 mg/kg of fresh sprouts), followed by sulforaphane (222.6 mg/kg) and 4-methylsulfinylbutylnitrile (63.0 mg/kg). Among 18 sulforaphane and related compounds synthesized (6 amines, 6 isothiocyanates, and 6 nitriles), 2 amines, 6 isothiocyanates, and

  从新鲜西兰花芽中制得的粗甲醇提取物依次用己烷，氯仿，乙酸乙酯和丁醇提取。从残余水层获得残余水部分。幽门螺杆菌有最大的抑制区（> 5 cm）依次用氯仿萃取液，己烷萃取液（5.03 cm），乙酸乙酯萃取液（4.90 cm），丁醇萃取液（3.10 cm）和粗甲醇萃取液（2.80 cm）显示任何抑制区。包括萝卜硫烷在内，在氯仿提取物中鉴定出了五种与萝卜硫烷相关的化合物，其中5-甲基亚磺酰基戊基腈的浓度最高（新鲜芽苗为475.7 mg / kg），其次是萝卜硫烷（222.6 mg / kg）和4-甲基亚磺酰基丁基腈。 （63.0 mg / kg）。在合成的18种萝卜硫烷和相关化合物（6种胺，6种异硫氰酸盐和6个腈）中，有2种胺，6种异硫氰酸盐和1个腈对幽门螺杆菌的抑制区大于5厘米拉紧。结果表明，西兰花芽可以作为药用物质的极佳食物来源。
• Über zwei einfache, optisch aktive Sulfoxyde
  作者：P. Karrer、N. J. Antia、R. Schwyzer

  DOI：10.1002/hlca.19510340522

  日期：——

  Es werden die racemischen und optisch aktiven Formen des Methyl-allyl-sulfoxyds (I) und des Methyl-[buten-(3)-yl-(1)]-sulfoxyds (II) dargestellt und untersucht.

  介绍和研究了甲基烯丙基亚砜（I）和甲基[丁烯-（3）-基-（1）]亚砜（II）的外消旋和旋光形式。
• Synthesis of Novel Analogs of Acetyl Coenzyme A: Mimics of Enzyme Reaction Intermediates
  作者：David P. Martin、Richard T. Bibart、Dale G. Drueckhammer

  DOI：10.1021/ja00090a014

  日期：1994.6

  An improved method for the synthesis of analogs of coenzyme A (CoA) and its thioesters, which are modified in the thiol or thioester moiety, has been developed using a combination of chemical and enzymatic reactions, The enzymes catalyzing the last two steps of CoA biosynthesis were used to prepare a CoA analog (1c) in which an amide bond is replaced by a thioester bond and the thiol group is replaced by a methyl group. Reaction of 1c with a primary amine in aqueous solution results in aminolysis of the thioester linkage to form the desired CoA analog. Reaction with different amines permits the introduction of a variety of functional groups in place of the nor mal thiol or thioester group. This methodology has been used in the synthesis of five new analogs of acetyl-CoA in which the thioester sulfur is replaced by a methylene group and the acetyl group is replaced by carboxylate (14a), nitro (14b), carboxamide (14c), methyl sulfoxide (14d), and methyl sulfone (14e) groups. 14a-c were designed to mimic the possible enolate or enol intermediate in the reaction of citrate synthase and related enzymes. 14a and 14c are potent inhibitors of citrate synthase, with K-i values 1000- and 570-fold lower than the K-m for acetyl-CoA, respectively. CD titrations indicate that 14a and 14c have low affinity for citrate synthase in the absence of oxaloacetate, consistent with their recognition as enol or enolate analogs. 14b is a poor inhibitor of citrate synthase, with affinity slightly lower than that for acetyl-CoA. These results are consistent with generation of the enol form of acetyl-CoA as the nucleophilic intermediate in the reaction of citrate synthase. 14d and 14e were designed to mimic the tetrahedral intermediate or transition state in the reaction of chloramphenicol acetyltransferase and related acetyl-CoA-dependent acetyltransferases. Both compounds are poor inhibitors of chloramphenicol acetyltransferase, with affinities slightly lower than that of acetyl-CoA, indicating that these compounds are not good mimics of the enzyme-bound tetrahedral intermediate or transition state.
• SCHULTZ; GLEIXNER, Archiv der Pharmazie, 1962, vol. 295 /67, p. 879 - 894
  作者：SCHULTZ、GLEIXNER

  DOI：——

  日期：——
• Squaramide-Based Pt(II) Complexes as Potential Oxygen-Regulated Light-Triggered Photocages
  作者：Kevin Morales、Katia G. Samper、Quim Peña、Jordi Hernando、Julia Lorenzo、Antonio Rodríguez-Diéguez、Mercè Capdevila、Marta Figueredo、Òscar Palacios、Pau Bayón

  DOI：10.1021/acs.inorgchem.8b02854

  日期：2018.12.17

  Two new squaramide-based platinum(II) complexes C1 and C2 have been synthesized and fully characterized. Their photoresponse has been assessed and is discussed. A remarkable enhancement in the DNA binding activity has been observed for both complexes, up on irradiation. For C2, the release of Pt(II) provoked by its irradiation has been studied. The response of C2 has been found to be regulated by the presence of oxygen. In vitro cytotoxicity tests show an enhancement in the activity of complex C2 after selective irradiation under hypoxic conditions. Resulting Pt(II) species have been isolated and characterized by various analytical methods establishing this type of squaramido-based complexes as a proof of concept for new Pt(II) photocages.