4-methyl-2(S)-<(triphenylmethyl)amino>-1-pentanal | 107600-13-5

• 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: 4-methyl-2(S)-<(triphenylmethyl)amino>-1-pentanal
• 英文别名: N-trityl-(S)-leucinal；N-tritylleucinal；(2S)-4-methyl-2-(tritylamino)pentanal
• CAS: 107600-13-5
• 化学式: C₂₅H₂₇NO
• 分子量: 357.495
• InChiKey: RCIIJMSUZHMCEU-DEOSSOPVSA-N

物化性质

• 沸点：
  466.9±33.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2(S)-<(triphenylmethyl)amino>-1-pentanal 在 palladium dihydroxide sodium hydroxide 、 sodium periodate 、 DOWEX-50-X₈ 、 氢气 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 35.08h， 生成 (7R)-7-isobutylperhydroazepin-2-one
  参考文献：
  名称：

  Evans, P. Andrew; Holmes, Andrew B.; Russell, Keith, Journal of the Chemical Society. Perkin transactions I, 1994, # 23, p. 3397 - 3410

  摘要：

  DOI：
• 作为产物：
  描述：

  L-亮氨醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 4-methyl-2(S)-<(triphenylmethyl)amino>-1-pentanal
  参考文献：
  名称：

  肾素抑制剂。包含新型血管紧张素原过渡态类似物的设计。（2R，3R，4R，5S）-5-氨基-3，4-二羟基-2-异丙基-7-甲基辛酸。

  摘要：

  2（R）-[5（R）-[1（S）-[（叔丁氧羰基氨基）氨基] -3-甲基丁基] -2,2-二甲基-4（R-二氧戊环）-的高立体选择性合成描述了3-甲基丁酸。这是一种适当保护的羧酸，可用作制备肾素抑制肽的中间体。血管紧张素原类似物如肽IX和X在易裂位点含有二肽等排物（2R，3R，4R，5S）-5-氨基-3,4-二羟基-2-异丙基-7-甲基辛酸残基人血浆肾素的有效抑制剂。该新型酸二羟基乙烯等排物中的二醇部分被建议充当过渡态类似物，并模仿在酶催化的肽键水解过程中形成的四面体中间体。

  DOI：

  10.1021/jm00389a004

文献信息

• Stereochemical control in the preparation of α-amino N-methylthiazolidine masked aldehydes used for peptide aldehydes synthesis
  作者：Christel Gros、Cyril Boulègue、Nathalie Galeotti、Gilles Niel、Patrick Jouin

  DOI：10.1016/s0040-4020(02)00115-1

  日期：2002.3

  Chiral N-methyl thiazolidines masked α-amino aldehydes are used for solid phase peptide aldehyde elongation. Contrary to N-Boc-protected α-amino aldehydes, N-trityl protection secures the chiral integrity of the incoming aldehyde chiral C1′ carbon atom during condensation of the amino aldehydes with l-cysteinyl residues. The Ac-Tyr-Val-Ala-Asp-H caspase inhibitor was prepared on a solid support starting

  手性N-甲基噻唑烷掩蔽的α-氨基醛用于固相肽醛的延伸。与N -Boc保护的α-氨基醛相反，N-三苯甲基保护可在氨基醛与1-半胱氨酰基残基缩合的过程中确保传入的醛手性C1'碳原子的手性完整性。从该掩盖天冬氨酸的N-三苯甲基-氨基噻唑烷开始，在固体支持物上制备Ac-Tyr-Val-Ala-Asp-H caspase抑制剂，以验证该过程。
• Novel renin inhibiting peptides having a dihydroxyethylene isostere transition state insert
  申请人：THE UPJOHN COMPANY

  公开号：EP0237202A2

  公开（公告）日：1987-09-16

  The present invention provides novel renin-inhibiting peptides of the formula X-A6-B7-C8-D9-E10-F11-G12-H13-I14-Z, wherein the E10-F11 moiety is a dihydroxyethylene isostere, X and Z are terminal groups, and the remaining variables are absent or are amino acid residues. Such inhibitors are useful for the control of hypertension.

  本发明提供了式X-A6-B7-C8-D9-E10-F11-G12-H13-I14-Z的新型肾素抑制肽，其中E10-F11分子是二羟基乙烯异构体，X和Z是末端基团，其余变量不存在或为氨基酸残基。 这种抑制剂可用于控制高血压。
• Liquid detergents containing a peptide trifluoromethyl ketone
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0583535A1

  公开（公告）日：1994-02-23

  Aqueous liquid detergent compositions are described which comprise a proteolytic enzyme wherein the proteolytic activity is reversibly inhibited by a peptide trifluoromethyl ketone.

  所述的水基液体洗涤剂组合物包含一种蛋白水解酶，其中蛋白水解酶的活性被一种肽三氟甲基酮可逆地抑制。
• New inhibitors of renin that contain novel phosphostatine Leu-Val replacements
  作者：Joseph F. Dellaria、Robert G. Maki、Herman H. Stein、Jerome Cohen、David Whittern、Kennan Marsh、Daniel J. Hoffman、Jacob J. Plattner、Thomas J. Perun

  DOI：10.1021/jm00164a011

  日期：1990.2

  A novel series of renin inhibitors based on the Phe8-His9-Leu10-Val11 substructure of renin's natural substrate, angiotensinogen, is reported. These inhibitors retain the Phe8-His9 portion of the native substructure and employ novel phosphostatine Leu10-Val11 replacements (LVRs). The phosphostatine LVRs were prepared by condensing a dialkyl phosphonate ester stabilized anion with either N-t-Boc-amino aldehydes or N-tritylamino aldehydes (derived from the corresponding amino acid). Structure-activity relationships at the Leu10 side chain revealed that the LVR derived from L-cyclohexylalanine provided a 130-fold boost in potency over the LVR derived from L-leucine. The dialkyl ester moiety was varied and a loss in potency was incurred when the alkyl ester was chain extended or alpha-branched; dimethyl esters provided optimum potency. The phosphonate moiety was replaced by a half-acid half-ester phosphonate and dimethylphosphinate; both replacements lead to a loss in potency. The more potent inhibitors (IC50 = 20-50 nM) were found to be selective inhibitors for renin over porcine pepsin and bovine cathepsin D (little or no inhibition was observed at 10(-5) M).
• Improved stereocontrolled synthesis of threo peptidyl epoxides
  作者：Amnon Albeck、Rachel Persky

  DOI：10.1021/jo00082a026

  日期：1994.2