N-methoxy-N-methyl-3-(tritylthio)propanamide | 150350-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-methoxy-N-methyl-3-(tritylthio)propanamide
• 英文别名: 3-[(Triphenylmethyl)thio]-N-methoxy-N-methylpropanamide；N-Methoxy-N-methyl-3-[(triphenylmethyl)sulfanyl]propanamide；N-methoxy-N-methyl-3-tritylsulfanylpropanamide
• CAS: 150350-27-9
• 化学式: C₂₄H₂₅NO₂S
• 分子量: 391.534
• InChiKey: ZCHQUCWZCHHZLS-UHFFFAOYSA-N

物化性质

• 沸点：
  493.7±47.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-3-(tritylthio)propanamide 在 lithium aluminium tetrahydride 作用下， 生成 3-(三苯甲硫基)丙醛
  参考文献：
  名称：

  Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

  摘要：

  A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.

  DOI：

  10.1021/acs.orglett.7b01324
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 3-(三苯甲硫基)丙醛 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到N-methoxy-N-methyl-3-(tritylthio)propanamide
  参考文献：
  名称：

  Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

  摘要：

  A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.

  DOI：

  10.1021/acs.orglett.7b01324

文献信息

• Heterocyclic inhibitors of farnesyl protein transferase
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0618221A3

  公开（公告）日：1995-02-15

  Inhibition of farnesyl protein transferase is effected by compounds of the formula its enantiomers, diastereomers, pharmaceutically acceptable salts, prodrugs or solvates thereof, wherein:    A₁ and A₂ are each independently H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, phenyl or substituted phenyl;    G₁ is S or O;    G₂ is H, -C(O)OH, -C(O)NH₂, 5-tetrazolyl, -C(O)N(R₇)OH or -CH₂OH;    X is O or R₈N;    Y and Z are each independently -CH₂- or -C(O)-;    R₁, R₂, R₃, R₄, R₅, R₆ and R₇ are each independently H or alkyl;    R₁ may also be alkanoyl,    R₁ and A₁ taken together may be -(CH₂)m;    R₈ is H, alkyl, phenyl, phenylalkyl, substituted phenyl, (substituted phenyl)alkyl or -C(O)R₉;   R₉ is H, alkyl, phenyl, phenylalkyl, substituted phenyl or (substituted phenyl)alkyl;    m is 3 or 4;    n is 0, 1 or 2;    p is 0, 1 or 2; and    q is 0 or 1, with the proviso that when p is 0, then q is also 0.

  该公式的化合物通过其对映体、非对映体、药用可接受的盐、前药或溶剂化合物来影响法尼基蛋白转移酶的抑制作用，其中： A₁和A₂分别独立地为H、烷基、取代烷基、环烷基、取代环烷基、苯基或取代苯基； G₁为S或O； G₂为H、-C(O)OH、-C(O)NH₂、5-四唑基、-C(O)N(R₇)OH或-CH₂OH； X为O或R₈N； Y和Z分别独立为-CH₂-或-C(O)-； R₁、R₂、R₃、R₄、R₅、R₆和R₇分别独立为H或烷基； R₁也可以是烷酰基， R₁和A₁一起可以是-(CH₂)m； R₈为H、烷基、苯基、苯基烷基、取代苯基、(取代苯基)烷基或-C(O)R₉； R₉为H、烷基、苯基、苯基烷基、取代苯基或(取代苯基)烷基； m为3或4； n为0、1或2； p为0、1或2；和 q为0或1，但当p为0时，q也为0。
• Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
  作者：Thimmalapura M. Vishwanatha、Enrico Bergamaschi、Alexander Dömling

  DOI：10.1021/acs.orglett.7b01324

  日期：2017.6.16

  A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.